cas 2444-36-2, 2-Chlorophenylacetic acid | Articles data

Articles about 2444-36-2Total 28 be found

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Smith,Fahey
p. 3391,3392
(1959)
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Alkali-modified heterogeneous Pd-catalyzed synthesis of acids, amides and esters from aryl halides using formic acid as the CO precursor
To establish an environmentally friendly green chemical process, we minimized and resolved a significant proportion of waste and hazards associated with conventional organic acids and molecular gases, such as carbon monoxide (CO). Herein, we report a facile and milder reaction procedure, using low temperatures/pressures and shorter reaction time for the carboxyl- and carbonylation of diverse arrays of aryl halides over a newly developed cationic Lewis-acid promoted Pd/Co3O4catalyst. Furthermore, the reaction proceeded in the absence of acid co-catalysts, and anhydrides for CO release. Catalyst reusability was achievedviascalable, safer, and practical reactions that provided moderate to high yields, paving the way for developing a novel environmentally benign method for synthesizing carboxylic acids, amides, and esters.
Fapojuwo, Dele Peter,Maqunga, Nomathamsanqa Prudence,Meijboom, Reinout,Mogudi, Batsile M.,Molokoane, Pule Petrus,Onisuru, Oluwatayo Racheal,Oseghale, Charles O.
p. 26937 - 26948
(2021/08/17)

Method for converting benzyl borate compounds into phenylacetic acid and derivatives thereof by carbon dioxide
The invention discloses a method for converting benzyl borate compounds into phenylacetic acid and derivatives thereof by carbon dioxide. The method comprises the steps: dissolving the benzyl borate compounds and an alkali in an organic solvent in the absence of a metal catalyst, introducing carbon dioxide into the reaction system, carrying out a reaction at the temperature of 50-150 DEG C for 3-72 hours, and acidifying to obtain phenylacetic acid or the derivatives thereof. The method is a green, simple and efficient method for synthesizing phenylacetic acid and the derivatives thereof, greenhouse gas carbon dioxide is used as a carbon source in the reaction, no transition metal catalyst is used, and the method is environmentally friendly, economical and high in efficiency.
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Paragraph 0038-0039

(2020/03/06)

Pd(OH)2/C, a Practical and Efficient Catalyst for the Carboxylation of Benzylic Bromides with Carbon Monoxide
A simple, efficient, cheap, and broadly applicable system for the carboxylation of benzylic bromides with carbon monoxide and water is reported. Upon simple reaction with only 2.5 wt % of Pearlman's catalyst and 10 mol % of tetrabutylammonium bromide in tetrahydrofuran at 110 °C for 4 h, a range of benzylic bromides can be smoothly converted to the corresponding arylacetic acids in good to excellent yields after simple extraction and acid-base wash. The reaction was found to be broadly applicable, scalable, and could be successfully extended to the use of ex situ-generated carbon monoxide and applied to the synthesis of the nonsteroidal anti-inflammatory drug diclofenac.
Wakuluk-Machado, Anne-Marie,Dewez, Damien F.,Baguia, Hajar,Imbratta, Miguel,Echeverria, Pierre-Georges,Evano, Gwilherm
p. 713 - 723
(2020/02/04)

Preparation method of phenylacetic acid type compound
The invention discloses a preparation method of a phenylacetic acid type compound. The preparation method of the phenylacetic acid type compound I comprises the following steps that in a solvent and aCO gas phase system, a benzyl halide type compound II, pyridine-2-cobalt carboxylate, palladium acetate and alkaline neutralizers take carbonylation reaction to obtain the phenylacetic acid type compound I. A mixed catalytic system has a synergistic effect; the whole use quantity of catalysts is greatly reduced. When the mixed catalyst is used, a better catalytic effect can be achieved; the characteristics of easily obtaining the catalyst, avoiding the production safety risk of toxic three wastes and the like, reducing the reaction pressure, realizing mild reaction conditions, reducing the production risk, facilitating the production and the like are realized. The formulas are shown in description.
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Paragraph 0092; 0093; 0094

(2019/02/21)

Electrogenerated Sm(II)-Catalyzed CO2 Activation for Carboxylation of Benzyl Halides
Sm(II)-catalyzed carboxylation of benzyl halides is reported through the electrochemical reduction of CO2. The transformation proceeds under mild reaction conditions to afford the corresponding phenylacetic acids in good to excellent yields. This user-friendly and operationally simple protocol represents an alternative to traditional strategies, which usually proceeds through the C(sp3)-halide activation pathway.
Bazzi, Sakna,Schulz, Emmanuelle,Mellah, Mohamed
supporting information
p. 10033 - 10037
(2019/12/24)

An improved method for the synthesis of phenylacetic acid derivatives via carbonylation
2,4-Dichlorophenylacetic acid is synthesized in high yield via the carbonylation of 2,4-dichlorobenzyl chloride, and various experimental conditions are evaluated. Xylene, bistriphenylphosphine palladium dichloride, tetraethylammonium chloride and sodium hydroxide in solution are added to the reaction system and held at 80 °C under a CO atmosphere. 2,4-Dichlorophenylacetic acid is obtained in a maximum yield of 95percent, and a mechanism for 2,4-dichlorobenzyl chloride carbonylation is proposed. The reaction system provides a mild, effective and novel means by which to prepare phenylacetic acid derivatives from their corresponding benzyl chloride derivatives.
Li, He,Zhang, Yijun,Liu, Dinghua,Liu, Xiaoqin
p. 548 - 552
(2019/11/13)

Synthetic method of fatty acid containing nitrogen heterocycle
The invention discloses a synthetic method of fatty acid containing nitrogen heterocycle. The synthetic method comprises the following steps: (S1) adding a heterocyclic compound with substitution of chloromethyl groups, a catalyst and a solvent DMF into a reaction kettle; (S2) introducing carbon dioxide to lead the pressure in the kettle to be 2-4MPa, adjusting and reacting for 10-16 hours at thetemperature of 40-50 DEG C; (S3) adding diluted hydrochloric acid into the reaction kettle to carry out acidification, using ethyl acetate for extraction, combining organic phases, carrying out rotaryevaporation to remove liquid, and further carrying out vacuum drying, thus obtaining the fatty acid containing nitrogen heterocycle. The synthetic method disclosed by the invention has the beneficialeffects that a one-pot method is adopted, the raw materials are easy to obtain, price is low, aftertreatment of products is also simpler, the universality for a substrate is also very high, and the promotion and application are easy.
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Paragraph 0042

(2018/07/30)

A General, Activator-Free Palladium-Catalyzed Synthesis of Arylacetic and Benzoic Acids from Formic Acid
A new catalyst for the carboxylative synthesis of arylacetic and benzoic acids using formic acid (HCOOH) as the CO surrogate was developed. In an improvement over previous work, CO is generated in situ without the need for any additional activators. Key to success was the use of a specific system consisting of palladium acetate and 1,2-bis((tert-butyl(2-pyridinyl)phosphinyl)methyl)benzene. The generality of this method is demonstrated by the synthesis of more than 30 carboxylic acids, including non-steroidal anti-inflammatory drugs (NSAIDs), under mild conditions in good yields.
Wang, Lin,Neumann, Helfried,Beller, Matthias
supporting information
p. 6910 - 6914
(2018/06/04)

Characterization of a new nitrilase from Hoeflea phototrophica DFL-43 for a two-step one-pot synthesis of (S)-β-amino acids
A nitrilase from Hoeflea phototrophica DFL-43 (HpN) demonstrating excellent catalytic activity towards benzoylacetonitrile was identified from a nitrilase tool-box, which was developed previously in our laboratory for (R)-o-chloromandelic acid synthesis from o-chloromandelonitrile. The HpN was overexpressed in Escherichia coli BL21 (DE3), purified to homogeneity by nickel column affinity chromatography, and its biochemical properties were studied. The HpN was very stable at 30–40?°C, and highly active over a wide range of pH values (pH 6.0–10.0). In addition, the HpN could tolerate against several hydrophilic organic solvents. Steady-state kinetics indicated that HpN was highly active towards benzoylacetonitrile, giving a KM of 4.2?mM and a kcat of 170?s?1, the latter of which is ca. fivefold higher than the highest record reported so far. A cascade reaction for the synthesis of optically pure (S)-β-phenylalanine from benzoylacetonitrile was developed by coupling HpN with an ω-transaminase from Polaromonas sp. JS666 in toluene-water biphasic reaction system using β-alanine as an amino donor. Various (S)-β-amino acids could be produced from benzoylacetonitrile derivatives with moderate to high conversions (73–99%) and excellent enantioselectivity (> 99% ee). These results are significantly advantageous over previous studies, indicating a great potential of this cascade reaction for the practical synthesis of (S)-β-phenylalanine in the future.
Zhang, Zhi-Jun,Cai, Rui-Feng,Xu, Jian-He
p. 6047 - 6056
(2018/05/15)

Preparation method of phenylacetic acid compound
The invention provides a preparation method of a phenylacetic acid compound. The method includes the steps of: subjecting a benzyl chloride compound to carbonylation under an assistant condition; and then adjusting the pH value to obtain a phenylacetic acid compound. Compared with other methods, the method provided by the invention has the advantages of easily available and cheap raw materials, high production efficiency, greatly alleviated environmental pollution and low cost, also improves the conversion rate, can acquire high purity product (with GC being greater than 99%), and the yield is about 90%. Therefore, the preparation method is convenient for industrial production.
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Paragraph 0056-0059; 0060-0063; 0064-0067; 0068-0071

(2017/08/28)

A method for the preparation of phenylacetic acid derivatives
The invention discloses a preparation method of a substituted phenylacetic acid derivative. The method comprises the following steps: 1, carrying out a sulfonylation reaction on substituted phenylglycine and sulfuryl chloride under the action of an alkali, and post-processing after completing the reaction to obtain an intermediate; and 2, carrying out a deamination reaction on the intermediate obtained in step 1 under the action of an organic acid and a reducing agent, and post-processing after completing the reaction to obtain the substituted phenylacetic acid derivative. The raw material phenylglycine used in the above route can be very easily purchased from the market, and is cheap and easily available. The preparation method has the advantages of short process route, mild reaction conditions, simple operation, high reaction yield and low total lost.
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Paragraph 0059; 0060; 0061; 0062

(2017/05/30)

Palladium-Catalyzed Carboxylation of Benzyl Chlorides with Atmospheric Carbon Dioxide in Combination with Manganese/Magnesium Chloride
An efficient direct carboxylation of a series of benzyl chlorides with CO2 catalyzed by Pd(OAc)2/dicyclohexyl (2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (SPhos) was developed to afford the corresponding phenylacetic acids in combination with Mn powder as a reducing reagent and MgCl2 as an indispensable additive. The reaction proceeded smoothly under 1 atm CO2. The application of Mn powder instead of a sensitive reducing reagent represents an operationally simple access to phenylacetic acids. Notably, MgCl2 is able to stabilize the (SPhos)2PdII(Bn)(Cl)(η1-CO2)(MgCl2) adduct and thus facilitates CO2 insertion into the PdII-C bond, which is supported by a DFT study. Specific effect: MgCl2 facilitates the direct insertion of CO2 into the PdII-C bond by stabilizing the PdII-CO2 adduct. With MgCl2 as an indispensable additive, the Pd-catalyzed carboxylation of various benzyl chlorides proceeded smoothly under 1 atm CO2, and the application of Mn powder instead of a sensitive reducing reagent makes this protocol an operationally simple access to phenylacetic acids.
Zhang, Shuai,Chen, Wei-Qiang,Yu, Ao,He, Liang-Nian
p. 3972 - 3977
(2016/01/26)

A high-throughput screening method for determining the substrate scope of nitrilases
Nitrile compounds are intermediates in the synthesis of pharmaceuticals such as atorvastatin. We have developed a chromogenic reagent to screen for nitrilase activity as an alternative to Nessler's reagent. It produces a semi-quantifiable blue colour and hydrolysis of 38 nitrile substrates by 23 nitrilases as cell-free extracts has been shown. This journal is
Black, Gary W.,Brown, Nicola L.,Perry, Justin J. B.,Randall, P. David,Turnbull, Graeme,Zhang, Meng
supporting information
p. 2660 - 2662
(2015/03/05)

PROCESS FOR SYNTHESIZING PHENYLACETIC ACID BY CARBONYLATION OF TOLUENE
A production process for substituted phenylacetic acids or ester analogues thereof is disclosed. In this process toluene or toluene substituted with various substituents, an alcohol, an oxidant and carbon monoxide are used as raw materials to obtain compounds comprising structure of phenylacetic acid ester or analogues thereof by catalysis of the complex catalyst formed from transition metal and ligand, and such compounds are hydrolyzed to obtain various substituted phenylacetic acid based compounds. This type of compounds and their derivatives serve as important fine chemicals used widely in the industries of pharmaceuticals, pesticides, perfume and the like.
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Paragraph 0018; 0066; 0067

(2013/11/19)

Ni-catalyzed direct carboxylation of benzyl halides with CO2
A novel Ni-catalyzed carboxylation of benzyl halides with CO2 has been developed. The described carboxylation reaction proceeds under mild conditions (atmospheric CO2 pressure) at room temperature. Unlike other routes for similar means, our method does not require well-defined and sensitive organometallic reagents and thus is a user-friendly and operationally simple protocol for assembling phenylacetic acids.
León, Thierry,Correa, Arkaitz,Martin, Ruben
supporting information
p. 1221 - 1224
(2013/03/14)

An efficiently cobalt-catalyzed carbonylative approach to phenylacetic acid derivatives
A highly efficient cobalt-catalyzed carbonylative approach to phenylacetic acid derivatives under one atmosphere pressure is reported. This methodology represents a useful extension of benzimidazole used as ligand in metal catalysis, and the catalytic mechanism has been proved by computer simulation. Notably, this new cobalt precatalyst, which promotes the carbonylation reaction dramatically and has already been used for scale-up experiment of phenylacetic acid derivatives.
She, Meng-Yao,Xiao, Da-Wei,Yin, Bing,Yang, Zheng,Liu, Ping,Li, Jian-Li,Shi, Zhen
p. 7264 - 7268
(2013/08/23)

Nitrile biotransformation by whole cells of Aspergillus sp. PTCC 5266
Aspergillus sp. PTCC 5266 exhibited nitrile-hydrating activity over a broad pH range from 6.0 to 10.0 at 26°C. It hydrated 4-nitrophenylacetonitrile, 2-chlorobenzonitrile and 3-chlorobenzonitrile to their corresponding carboxylic acids and amides, while benzyl cyanide, benzonitrile, 4-tolunitrile, cyclohexanecarbonitrile, 4-chlorobutyronitrile and isobutyronitrile gave carboxylic acids as the sole products. The maximum whole-cell nitrile-hydrating activity was observed at pH 7.0.
Yousefi,Mohammadi,Habibi,Cheraghi
experimental part
p. 54 - 59
(2012/03/10)

Direct addition of functionalized organozinc reagents to carbon dioxide, ketones, and aldehydes in the presence of MgCl2
A variety of functionalized organozinc reagents undergo smooth addition reactions at ambient temperature to carbon dioxide, ketones, and aldehydes in the presence of stoichiometric amounts of MgCl2. Several reactions were performed on a 20 mmol scale. Georg Thieme Verlag Stuttgart · New York.
Bernhardt, Sebastian,Metzger, Albrecht,Knochel, Paul
experimental part
p. 3802 - 3810
(2011/01/12)

Exceptionally simple catalytic system for the carbonylation of benzyl halides
A ligand-less catalytic system, Pd(OAc)2 immobilized in NBu4Hal melt is suggested for the synthesis of arylacetic acids by the carbonylation of benzyl bromides.
Lapidus, Albert L.,Eliseev, Oleg L.,Bondarenko, Tatyana N.,Chau, Nguen H.,Kazantsev, Ruslan V.
scheme or table
p. 256 - 257
(2010/01/18)

An efficient method for one-carbon elongation of aryl aldehydes via their dibromoalkene derivatives
Various aryl aldehydes were efficiently converted into one-carbon extended aryl acetamides or aryl acetic acids through the reaction of their dibromoalkene derivatives with pyrrolidine in the presence of water under very mild conditions.
Huh, Dal Ho,Jeong, Ji Sang,Lee, Hee Bong,Ryu, Hoejin,Kim, Young Gyu
p. 9925 - 9932
(2007/10/03)

Quinolones as gonadotropin releasing hormone (GnRH) antagonists: Simultaneous optimization of the C(3)-aryl and C(6)-substituents
A series of 3-arylquinolones was prepared and evaluated for their ability to act as gonadotropin releasing hormone (GnRH) antagonists. A variety of substitution patterns of the 3-aryl substituent are described. The 3,4,5-trimethylphenyl substituent (23h) was found to be optimal. (C) 2000 Elsevier Science Ltd. All rights reserved.
Young, Jonathan R.,Huang, Song X.,Chen, Irene,Walsh, Thomas F.,DeVita, Robert J.,Wyvratt Jr., Matthew J.,Goulet, Mark T.,Ren, Ning,Lo, Jane,Yang, Yi Tien,Yudkovitz, Joel B.,Cheng, Kang,Smith, Roy G.
p. 1723 - 1727
(2007/10/03)

Efficient synthesis of α-enaminophosphonates in the series of piperidine and morpholine: Examples of synthetic applications
Various α-piperidino or α-morpholino alkenylphosphonates are conveniently prepared from the related α-hetero-substituted methylphosphonates, through a Peterson olefination process, which can be easily adapted for a direct homologation of aldehydes into carboxylic acids. An efficient synthesis of α-piperidino or α-morpholino alkylphosphonates and phosphonic acids is proposed.
Dufrechou,Combret,Malhiac,Collignon
p. 1 - 14
(2007/10/03)

On the Conformation of the Substrate Binding to the Active Site during the Course of Enzymatic Decarboxylation
The activation parameters of the enzymatic decarboxylation of malonic acid derivatives catalyzed by arylmalonate decarboxylase (AMDase) were obtained by means of kinetics. In order to understand the conformation of the substrate at the transition state, the activation entropy (ΔS?) for indane-1,1-dicarboxylic acid, a representative molecule that is conformationally restricted, was compared with those of phenylmalonic acid and ortho-chlorophenylmalonic acid, of which the aromatic ring can freely rotate. The obtained value for the former molecule was about 10 cal mol-1 K-1 smaller than those of the latter compounds, clearly indicating that a conformationally restricted substrate, such as the indane derivative, is entropically advantageous for enzymatic decarboxylation. These kinetic studies evidently disclose that the conformation of the substrate at the transition state in the course of AMDase-catalyzed decarboxylation should be synperiplanar with regard to ortho- and α-substituents.
Kawasaki, Takayasu,Horimai, Emiko,Ohta, Hiromichi
p. 3591 - 3594
(2007/10/03)

Cobalt carbonyl catalyzed carbonylation of benzal bromides by phase transfer catalysis
The reaction of benzal bromides with CO (1 atm) in a binary system (aq.KOH/C6H6) in the presence of a catalytic amount of Co2(CO)8 together with benzyltriethylammonium chloride as a phase transfer catalyst for 8 h at room temperature gives the corresponding carboxylic acids in good to excellent yields.
Shim, Sang Chul,Doh, Chil Hoon,Park, Woo Hyun,Kwon, Young Gil,Lee, Hyung Soo
p. 419 - 421
(2007/10/02)

Lanthanide-Promoted and Nickel Cyanide Catalyzed Carbonylation Reactions under Phase-Transfer Conditions
The nickel cyanide and phase transfer catalyzed carbonylation of benzyl chlorides is promoted by lanthanide salts .This simple reaction is sensitive to the concentration of the lanthanide compound, sodium hydroxide, quaternary ammonium salt, and nickel catalyst.The nature of the organic phase and phase transfer agent also influences the reaction rate.The acceleration of the reaction may be a consequence of coordination of a nickel cyanide nitrogen lone pair to the lanthanide salt.
Amer, Ibrahim,Alper, Howard
p. 927 - 930
(2007/10/02)

Preparation of optically active carboxylic acids
Optically active carboxylic acids STR1 where R1 is an organic radical which is linked to the asymmetric C' atom via a carbon atom and R2 is one of the radicals R1 (but not the same radical), halogen or an organic radical which is bonded to the asymmetric C' atom via an oxygen atom, are prepared by reacting a ketene II STR2 with an alcohol in a homogeneous liquid phase in the presence of a tertiary amine III and then converting the resulting ester into the acid, using an optically active alcohol IV.
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(2008/06/13)

Process for the preparation of carboxylic acids and N-tert.-alkylamines
Carboxylic acids and N-t.-alkylamines can be prepared simultaneously by the alkaline pressure hydrolysis of N-t.-alkyl carboxylic acid amides. A 5 to 50% strength by weight aqueous solution of an alkali metal hydroxide is employed for this purpose in an amount of 1.0 to 1.3 mols per mol of the amide. The process is carried out at 200° to 350° C.
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(2008/06/13)

Process for production of o-(2,6-dichloroanilino)-phenylacetic acid
There is provided a process for production of o-(2,6-dichloroanilino)phenylacetic acid or a salt thereof by reacting o-chlorophenylacetic acid or an alkali metal salt thereof with 2,6-dichloroaniline in the presence of a base and at least 0.5 mol of a copper catalyst per mol of o-chlorophenylacetic acid in a polar solvent.
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(2008/06/13)