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A Practical Procedure for Regioselective Bromination of Anilines
A highly practical procedure for the preparation of bromoanilines by using copper-catalyzed oxidative bromination has been developed. Treatment of free anilines with readily available NaBr and Na 2S 2O 8in the presence of a catalytic amount of CuSO 4·5H 2O enabled regioselective bromination.
Takahashi, Yusuke,Seki, Masahiko
p. 1828 - 1832
(2021/04/15)

Aryl halide and synthesis method and application thereof
The invention discloses a synthesis method of aryl halides (including aryl bromide shown as a formula (2) and aryl iodide shown as a formula (3)). All the systems are carried out in an air atmosphere,visible light is utilized to excite a substrate or a photosensitizer to catalyze the reaction; and in a reaction solvent, when aromatic hydrocarbon shown in the formula (1) and sodium bromide serve as raw materials, aryl bromide shown in the formula (2) is obtained through a reaction under the auxiliary action of an additive (protonic acid); or when aromatic hydrocarbon shown in the formula (1) and sodium iodide are used as raw materials, under the auxiliary action of an additive (protonic acid), aryl iodide shown in the formula (3) is obtained through reaction. The synthesis method has the advantages of cheap and accessible raw materials, simple reaction operation and mild reaction conditions. The method is compatible with the arylamine which is liable to be oxidized. The invention provides a new method for the synthesis of aryl halides, realizes the amplification of basic chemicals aryl halides including aryl bromide shown in the formula (2) and aryl iodide shown in the formula (3),and has wide application prospect and practical value.
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Paragraph 0061-0063

(2020/06/02)

Visible-light-promoted oxidative halogenation of (hetero)arenes
Organic halides are critical building blocks that participate in various cross-coupling reactions. Furthermore, they widely exist as natural products and artificial molecules in drugs with important physiological activities. Although halogenation has been well studied, to the best of our knowledge, studies focussing on sensitive systems (e.g.aryl amines) have not been reported. Herein, we describe a compatible oxidative halogenation of (hetero)arenes with air as the oxidant and halide ions as halide sources under ambient conditions (visible light, air, aqueous system, room temperature, and normal pressure). Moreover, this protocol is practically feasible for gram-scale synthesis, showing potential for industrial application.
Jiang, Xuefeng,Li, Yiming,Lu, Lingling
supporting information
p. 5989 - 5994
(2020/10/18)

A metal-free aerobic oxidative bromination of anilines and aryl ketones with 2-methylpyridinium nitrate as a reusable ionic liquid
An aerobic oxidative bromination of anilines and aryl ketones catalyzed by recyclable 2-methylpyridinium nitrate ionic liquid is achieved in water using hydrobromic acid as the bromine source and molecular oxygen as the oxidant. The catalytic system shows good efficiency and atom economy.
Li, Ming-Fang,Wang, Jian,Ke, Yong-Xin,Pan, Song-Cheng,Yin, Hong,Du, Wenting,Li, Jing-Hua
p. 267 - 270
(2020/01/08)

Sodium sulfate-hydrogen peroxide-sodium chloride adduct: selective protocol for the oxidative bromination, iodination and temperature dependent oxidation of sulfides to sulfoxides and sulfones
The regioselective bromination and iodination of unprotected aromatic primary amines using enclathrated hydrogen peroxide as an oxidant under mild conditions has been developed, in which potassium bromide (KBr) and potassium iodide (KI) were used as brominating and iodinating agents, respectively. The adduct shows not only regioselectivity for para- or ortho-isomers but also a remarkable chemoselectivity for monobromination. Selective oxidation of sulfides to sulfoxides and sulfones has also been studied and good to excellent yields of the desired products were obtained. Acetic acid was found to be the solvent of choice for these reactions. This simple method represents an ecologically benign and alternative pathway for the oxidative halogenation of anilines and the oxidation of sulfides to sulfoxides and sulfones.
Gayakwad, Eknath M.,Patel, Khushbu P.,Shankarling, Ganapati S.
supporting information
p. 6001 - 6009
(2019/04/17)

Green synthesis of bromo organic molecules and investigations on their antibacterial properties: An experimental and computational approach
A simple, environmentally benign methodology has been developed to synthesize some bromoorganic compounds which have potential as antimicrobial agents. The required compounds were obtained through microwave (MW) irradiation, on-water reactions and using cetyltrimethylammonium tribromide (CTMATB) as the bromine source. The high yield of the product could be achieved within short reaction times, thus representing the main attribute of the present synthetic approach. The compounds were evaluated for in vitro antibacterial activity against Escherichia coli, Klebsiella pneumoniae, Staphylococcus aureus and Bacillus subtilis. Further, in silico studies were carried out to elucidate the interactions of the compounds with the bacterial proteins.
Longkumer, Naruti,Richa, Kikoleho,Karmaker, Rituparna,Kuotsu, Visekhonuo,Supong, Aola,Jamir, Latonglila,Bharali, Pranjal,Sinha, Upasana Bora
p. 276 - 283
(2019/07/12)

Visible-light photocatalytic activation of N-chlorosuccinimide by organic dyes for the chlorination of arenes and heteroarenes
A variety of arenes and heteroarenes are chlorinated in moderate to excellent yields using N-chlorosuccinimide (NCS) under visible-light activated conditions. A screening of known organic dye photocatalysts resulted in the identification of methylene green as the most efficient catalyst to use with NCS. According to mechanistic studies described within, the reaction is speculated to proceed via a single electron oxidation of NCS utilizing methylene green under visible-light photoredox pathway. The photo-oxidation of NCS amplifies the electrophilicity of the chlorine atom of the NCS, thus leading to enhanced reactivity as a chlorinating reagent with aromatic substrates.
Rogers, David A.,Gallegos, Jillian M.,Hopkins, Megan D.,Lignieres, Austin A.,Pitzel, Amy K.,Lamar, Angus A.
(2019/08/12)

A Visible Light-Mediated Regioselective Halogenation of Anilides and Quinolines by Using a Heterogeneous Cu-MnO Catalyst
A simple and practical heterogeneous Cu-MnO catalyzed regioselective halogenation of anilides and quinolines under irradiation with household 40 W incandescent lamp was developed. This method uses a recyclable Cu-MnO catalyst, acetonitrile as an industrially friendly solvent, and economic N-halo succinimides as a halogenating source. The reaction is scalable and well tolerated with a broad range of functional groups.
Singh, Harshvardhan,Sen, Chiranjit,Sahoo, Tapan,Ghosh, Subhash Chandra
p. 4748 - 4753
(2018/09/06)

Method for synthesizing monobrominated aniline compound
The invention discloses a method for synthesizing a monobrominated aniline compound. The method comprises the following steps: by taking an aniline compound as a raw material, and taking zinc aluminum hydrotalcite ZnAl-BrO3-LDHs with a bromate inserted layer and an alkali metal bromide as bromine sources in a mixed solvent of water and an organic solvent, reacting for 1-3h at 10-50 DEG C; after ending the reaction, extracting a reaction mixed solution A by using dichloromethane; adding a column chromatography silica gel into dichloromethane phase; removing the solvent in the manner of reduced pressure distillation; and acquiring a mono-bromination objective product in the manner of column chromatography separation by using an eluent composed of petroleum ether and ethyl acetate at the ratio of 10:1. The invention realizes a high-selectivity oxidative bromination method by adopting an aniline compound under the effects of ZnAl-BrO3-LDHs and potassium bromide; the monobrominated aniline compound is prepared; the reaction popularity is high and the raw material is low in cost and is easily acquired; the reaction condition is mild; the reaction yield is high; the atom utilization ratio is high; and the chemical selectivity is excellent and the environment is protected.
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Paragraph 0040; 0041; 0042; 0043

(2017/09/26)

Recyclable ionic liquid iodinating reagent for solvent free, regioselective iodination of activated aromatic and heteroaromatic amines
This article describes a simple, efficient method for iodination of activated aromatic and heteroaromatic amines using recyclable 1-butyl-3-methylpyridinium dichloroiodate (BMPDCI) as an ionic liquid iodinating reagent, in the absence of any solvent. The main advantages are a simple efficient procedure, good yields and no need for any base/toxic heavy metals, or oxidizing agents. The ionic liquid was recovered and recycled in five subsequent reactions, without much loss of activity. This method was applied for the synthesis of the antiprotozoal drug iodoquinol and the antifungal drug clioquinol.
Deshmukh, Amarsinh,Gore, Babasaheb,Thulasiram, Hirekodathakallu V.,Swamy, Vincent P.
p. 88311 - 88315
(2015/11/09)

Aerobic oxidation and oxidative bromination in aqueous medium using polymer anchored oxovanadium complex
Polymer anchored oxovanadium catalyst was synthesized and characterized. Its catalytic activity was evaluated for the oxidation of various primary and secondary alcohols with molecular oxygen under mild reaction conditions. This catalyst was also effective for the oxidative bromination reaction of organic substrates with 90-100% selectivity of mono substituted products with H 2O2/KBr at room temperature. The above reactions require low temperature, short time period and most importantly all the above reactions occur in aqueous medium. The developed catalyst can be facilely recovered and reused six times without significant decrease in activity and selectivity. 2014 Elsevier B.V. All rights reserved.
Islam, Sk. Manirul,Molla, Rostam Ali,Roy, Anupam Singha,Ghosh, Kajari,Salam, Noor,Iqubal, Md. Asif,Tuhina
p. 169 - 178
(2014/05/06)

Poly(4-vinylpyridinium bromochromate): An efficient reagent for bromination of aromatic compounds
A simple and efficient method for the bromination of various aromatic compounds by using poly(4-vinylpyridinium bromochromate) is reported. This method has several advantages such as good selectivity between ortho and para positions of aromatic compounds, simple workup, short reaction times, and high yields of the products.
Albadi, Jalal,Tajik, Hassan,Keshavarz, Mosadegh,Abedini, Masoumeh
p. 179 - 181
(2013/07/27)

A facile, regioselective and controllable bromination of aromatic amines using a CuBr2/Oxone system
A combination of cupric bromide and Oxone serves as a facile, mild and effective reagent for the bromination of aromatic amines. Primary, secondary and tertiary aromatic amines are all suitable substrates. The reaction possesses high regioselectivity and functional group tolerance, and mono- and multi-brominated products can be obtained controllably in moderate to excellent yields. The Royal Society of Chemistry 2013.
Li, Xin-Le,Wu, Wei,Fan, Xin-Heng,Yang, Lian-Ming
p. 12091 - 12095
(2013/09/02)

Green, mild and efficient bromination of aromatic compounds by HBr promoted by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane in water as a solvent
A combination of HBr and trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane as a new and powerful oxidant was found effective for facile bromination of different aromatic compounds at room temperature in water as a green solvent. Mild reaction conditions, high selectivity and yield, high reaction rate and non-toxicity are some of the major advantages of this synthetic protocol.
Khosravi, Kaveh,Kazemi, Samira
experimental part
p. 387 - 390
(2012/05/20)

Regioselective bromination and iodination of aromatic substrates promoted by trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane
Selective and efficient bromination and iodination of aromatic compounds by ammonium bromide and ammonium iodide, respectively, under promotion of trans-3,5-dihydroperoxy-3,5-dimethyl-1,2-dioxolane have been explored. Mild reaction conditions, high selectivity and yield, and high reaction rate are some of the major advantages of this synthetic method.
Azarifar, Davood,Khosravi, Kaveh,Najminejad, Zohreh,Soleimani, Khadijeh
experimental part
p. 321 - 326
(2012/08/14)

Synthesis, catalytic oxidation and oxidative bromination reaction of a reusable polymer anchored oxovanadium(IV) complex
Polymer anchored oxovanadium catalyst was synthesized and characterized. The solid catalyst was characterized by Fourier transform infrared spectroscopy (FT-IR), UV-vis diffuse reflectance spectroscopy (DRS), thermogravimetric analysis (TGA) and scanning electron microscope (SEM). Its catalytic activity was evaluated for the oxidation of various alkenes, sulfides and aromatic alcohols with 30% H2O2 under mild reaction conditions. This catalyst was also effective for the oxidative bromination reaction of organic substrates with 80-100% selectivity of mono substituted products with H2O2/KBr at room temperature. The above reactions require minimum amount of H2O2, short time period and most importantly all the above reactions occur in aqueous medium. The developed catalyst can be facilely recovered and reused six times without significant decrease in activity and selectivity. This result confirms that the polymer anchored complex was not leached during the reaction, suggesting the true heterogeneous nature of the catalyst.
Islam, Sk. Manirul,Roy, Anupam Singha,Mondal, Paramita,Salam, Noor
experimental part
p. 38 - 48
(2012/05/21)

Selective oxidation of sulfides and oxidative bromination of organic substrates catalyzed by polymer anchored Cu(II) complex
A new polymer-anchored Cu(II) complex has been synthesized and characterized. The catalytic performance of the complex has been tested for the oxidation of sulfides and in oxidative bromination reaction with hydrogen peroxide as the oxidant. Sulfides have been selectively oxidized to the corresponding sulfoxides in excellent yields and in the presence of KBr as the bromine source, organic substrates have been selectively converted to mono bromo substituted compounds using polymer-anchored Cu(II) catalyst. This catalyst showed excellent catalytic activity, high selectivity, and recyclability. The polymer-anchored Cu(II) catalyst could be easily recovered by filtration and reused more than five times without appreciable loss of its initial activity.
Islam,Roy, Anupam Singha,Mondal, Paramita,Tuhina, Kazi,Mobarak, Manir,Mondal, John
supporting information; experimental part
p. 127 - 131
(2012/01/17)

Identification of bromination products of chloro-substituted anilines in aqueous environment by gas chromatography
To reduce the detection limits of aniline and its various chloroderivatives (all isomers of mono- and dichloroanilines, 2,4,5 -, 2,4,6-, and 3,4,5-trichloroanilines, pentachloroaniline) in aqueous media we suggested bromination reaction, followed by gas chromatographic definition bromo derivatives of chloroanilines on a selective electron capture detector. To identify the products of bromination of chloroaniline in combination with mass-spectrometric data we used chromatographic retention indices on standard nonpolar polydimethylsiloxane stationary phase that was determined for 50 compounds in this class. The technique of identifying bromoderivatives of chloroaniline in water was developed at the gas-chromatographic analysis in the selective electron capture detector. To improve the reliability of the identification of additional bromoderivatives of chloroanilines we obtained their trifluoroacetyl derivatives.
Gruzdev,Filippova,Zenkevich,Kondratenok
experimental part
p. 1748 - 1759
(2012/02/15)

An efficient method for aryl nitro reduction and cleavage of azo compounds using iron powder/calcium chloride
A novel, efficient Fe/CaCl2 system is revealed for the reduction of nitroarenes and reductive cleavage of azo compounds by catalytic transfer hydrogenation (CTH). The selective reduction of nitro compounds in the presence of sensitive functional groups including halides, carbonyl, hydroxyl, aldehyde, methyl, methoxy, acetyl, nitrile, and ester substituents with an excellent yields is reported. The simple experimental procedure and easy purification make the protocol advantageous
Chandrappa,Vinaya,Ramakrishnappa,Rangappa
experimental part
p. 3019 - 3022
(2011/03/17)

Discovery of potent and selective urea-based ROCK inhibitors and their effects on intraocular pressure in rats
A series of urea-based Rho kinase (ROCK) inhibitors were designed and evaluated. The discovered compounds had excellent enzyme and cellular potency, high kinase selectivity, high aqueous solubility, good porcine corneal penetration, and appropriate DMPK profiles for topical applications as antiglaucoma therapeutics.
Yin, Yan,Cameron, Michael D.,Lin, Li,Khan, Susan,Schroeter, Thomas,Grant, Wayne,Pocas, Jennifer,Chen, Yen Ting,Schuerer, Stephan,Pachori, Alok,Lograsso, Philip,Feng, Yangbo
scheme or table
p. 175 - 179
(2010/10/21)

Effect of structural factors and solvent nature in bromination of anilines
Reaction of electrophilic bromination of aniline containing various ortho, meta, and para substituents in the aromatic ring was studied. The optimal conditions for synthesis of mono-, di-, tri-, and tetrabromo derivatives of aniline and brominated analog of Aniline Black were found.
Bagmanov
experimental part
p. 1570 - 1576
(2011/06/20)

Regioselective, photochemical bromination of aromatic compounds using N-bromosuccinimide
Regioselective nuclear bromination of aromatic compounds is investigated with N-bromosuccinimide as the brominating agent under UV irradiation to afford the corresponding brominated compounds. The reaction proceeds at ambient temperature (30 ± 2 °C) without any catalyst. In most of the reactions, regioselectively mono-brominated products are obtained in good to high yields. The conversion and selectivity for bromination depend on the nature of the substituent on the aromatic ring.
Chhattise, Prakash K.,Ramaswamy,Waghmode, Suresh B.
p. 189 - 194
(2008/03/30)

A convenient and regioselective oxidative bromination of electron-rich aromatic rings using potassium bromide and benzyltriphenylphosphonium peroxymonosulfate under nearly neutral reaction conditions
Regioselective oxidative bromination of electron-rich aromatic rings has been studied using potassium bromide as a bromine source in the presence of benzyltriphenylphosphonium peroxymonosulfate as oxidant under nearly neutral reaction conditions. In most cases we obtained monobrominated derivatives regioselectively and in good to high yields without the aid of strong acids.
Adibi, Hadi,Hajipour, Abdol R.,Hashemi, Majid
p. 1255 - 1259
(2007/10/03)

Regioselective and high-yielding bromination of aromatic compounds using hexamethylenetetramine-bromine
A regioselective and highly efficient method for bromination of aromatic compounds in the presence of a stoichiometric amount of hexamethylenetetramine- bromine (HMTAB) as an efficient reagent in dichloromethane is reported. The selectivity depends on the temperature and nature of the substituent on the substrate. The reactivity of this reagent was increased by supporting it to silica gel for bromination of less activated compounds.
Heravi, Majid M.,Abdolhosseini, Nafiseh,Oskooie, Hossein A.
p. 8959 - 8963
(2007/10/03)

Novel bromination method for anilines and anisoles using NH 4Br/H2O2 in CH3COOH
A simple, efficient, regioselective, environmentally safe, and economical method for the oxybromination of anilines and anisoles without catalyst is reported. The electrophilic substitution of bromine generated in situ from ammonium bromide as a bromine source and hydrogen peroxide as an oxidant for the first time.
Krishna Mohan,Narender,Srinivasu,Kulkarni,Raghavan
p. 2143 - 2152
(2007/10/03)

Processes for the preparation of hydratropic acids
Novel processes for making arylpropionic acids are described. One process comprises carboxylating particular Grignard compounds which are the products of a catalyzed reaction between corresponding arylmagnesium bromides and ethylene. Furthermore, the reaction making the particular Grignard compounds is itself novel. Also, an improved method is disclosed for making coupled aryl compounds useful as intermediates for making compounds having a pharmaceutical use. For example, particular biaryls may be used to make some of the Grignard compounds herein from which the arylpropionic acids are made. Finally, an improved bromination is disclosed giving high yields of 4-bromo-2-fluoroaniline, which is thereafter coupled with benzene, then used to make the arylmagnesium bromide reacted with ethylene to obtain the particular Grignard compound and subsequent desired arylpropionic acid, i.e. 2-(2-fluoro-4-biphenylyl)propionic acid.
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(2008/06/13)

Selective halogenation of 2-fluoroaniline
Novel processes for making arylpropionic acids are described. One process comprises carboxylating particular Grignard compounds which are the products of a catalyzed reaction between corresponding arylmagnesium bromides and ethylene. Furthermore, the reaction making the particular Grignard compounds is itself novel. Also, an improved method is disclosed for making coupled aryl compounds useful as intermediates for making compounds having a pharmaceutical use. For example, particular biaryls may be used to make some of the Grignard compounds herein from which the arylpropionic acids are made. Finally, an improved bromination is disclosed giving high yields of 4-bromo-2-fluoroaniline, which is thereafter coupled with benzene, then used to make the arylmagnesium bromide reacted with ethylene to obtain the particular Grignard compound and subsequent desired arylpropionic acid, i.e. 2-(2-fluoro-4-biphenylyl)propionic acid.
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(2008/06/13)

Mesoionic Compounds. Part 8. Acid-catalysed Hydrolysis of Aryloxatriazoles
The acid-catalysed hydrolyses of some 3-(para-substituted phenyl)oxatriazoles have been studied in aqueous solution of mineral acids at 120 deg C.Analyses of the data by Bunnett, Bunnett-Olsen, and excess acidity criteria are consistent with a gradual changeover from an A-2 mechanism at low acid concentration to a predominantly A-1 mechanism at high acidities.Values of pKBH+ of these compounds in sulphuric acid have been determined.
Said, Zainuddin,Tillett, John G.
p. 701 - 706
(2007/10/02)