cas 5326-34-1, 4-Bromo-3-nitrotoluene | Articles data

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Nitration of deactivated aromatic compounds via mechanochemical reaction
A variety of deactivated arenes were nitrated to their corresponding nitro derivatives in excellent yields under high-speed ball milling condition using Fe(NO3)3·9H2O/P2O5 as nitrating reagent. A radical involved mechanism was proposed for this facial, eco-friendly, safe, and effective nitration reaction.
Wu, Jian-Wei,Zhang, Pu,Guo, Zhi-Xin
supporting information

(2021/05/05)

Dehydroxyalkylative halogenation of C(aryl)-C bonds of aryl alcohols
We herein report Cu mediated side-directed dehydroxyalkylative halogenation of aryl alcohols. C(aryl)-C bonds of aryl alcohols were effectively cleaved, affording the corresponding aryl chlorides, bromides and iodides in excellent yields. Aryl alcohols could serve as both aromatic electrophilic and radical synthetic equivalents during the reaction.
Liu, Mingyang,Zhang, Zhanrong,Liu, Huizhen,Wu, Tianbin,Han, Buxing
supporting information
p. 7120 - 7123
(2020/07/14)

Inexpensive NaX (X = I, Br, Cl) as a halogen donor in the practical Ag/Cu-mediated decarboxylative halogenation of aryl carboxylic acids under aerobic conditions
Versatile and practical Ag/Cu-mediated decarboxylative halogenation between readily available aryl carboxylic acids and abundant NaX (X = I, Br, Cl) has been achieved under aerobic conditions in moderate to good yields. The halodecarboxylation is shown to be an effective strategy for S-containing heteroaromatic carboxylic acid and benzoic acids with nitro, chloro and methoxyl substituents at the ortho position. A gram-scale reaction and a three-step procedure to synthesize iniparib have been performed to evaluate the practicality of this protocol. A preliminary mechanistic investigation indicates that Cu plays a vital role and a radical pathway is involved in the transformation.
Fu, Zhengjiang,Jiang, Ligao,Zuo, Qianming,Li, Zhaojie,Liu, Yanzhu,Wei, Zhenhong,Cai, Hu
supporting information
p. 5416 - 5421
(2018/08/12)

Synthetic method of aryl halide taking aryl carboxylic acid as raw material
A synthetic method of an aryl halide taking aryl carboxylic acid as a raw material is characterized in that a corresponding aryl halide is formed by carrying out substitution reaction on an aryl carboxylic acid compound and haloid salt MX in an organic solvent under the condition that oxygen, a silver catalyst, a copper additive and a bidentate nitrogen ligand exist, wherein M in MX represents alkali metal or alkaline earth metal, and X represents F, Cl, Br or I. Compared with a conventional aryl halide synthetic method, the synthetic method disclosed by the invention has the obvious advantages that reaction raw materials (comprising aryl carboxylic acid and MX) are cheap and easy to obtain, the using amount of a metal catalyst is small, pollution to the environment when the oxygen is used as an oxidant is the smallest, good tolerance to various functional groups on an aromatic ring is obtained, the yield is high, and the like. The synthetic method disclosed by the invention can be widely applied to synthesis in the fields of medicine, materials, natural products and the like in industry and academia.
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Paragraph 0091

(2018/01/03)

Decarboxylative Halogenation and Cyanation of Electron-Deficient Aryl Carboxylic Acids via Cu Mediator as Well as Electron-Rich Ones through Pd Catalyst under Aerobic Conditions
Simple strategies for decarboxylative functionalizations of electron-deficient benzoic acids via using Cu(I) as promoter and electron-rich ones by employing Pd(II) as catalyst under aerobic conditions have been established, which lead to smooth synthesis of aryl halides (-I, Br, and Cl) through the decarboxylative functionalization of benzoic acids with readily available halogen sources CuX (X = I, Br, Cl), and easy preparation of benzonitriles from decarboxylative cyanation of aryl carboxylic acids with nontoxic and low-cost K4Fe(CN)6 under an oxygen atmosphere for the first time.
Fu, Zhengjiang,Li, Zhaojie,Song, Yuanyuan,Yang, Ruchun,Liu, Yanzhu,Cai, Hu
p. 2794 - 2803
(2016/04/26)

Selective activation of enantiotopic C(sp3)-hydrogen by means of chiral phosphoric acid: Asymmetric synthesis of tetrahydroquinoline derivatives
Chiral phosphoric acid-catalyzed asymmetric C-H functionalization has been achieved. In this process, enantiotopic C(sp3)-hydrogen is selectively activated by chiral phosphoric acid to afford tetrahydroquinoline derivatives with excellent enantioselectivities (up to 97% ee).
Mori, Keiji,Ehara, Kensuke,Kurihara, Kazuki,Akiyama, Takahiko
supporting information; experimental part
p. 6166 - 6169
(2011/06/21)

Efficient one-pot transformation of aminoarenes to haloarenes using halodimethylisulfonium halides generated in situ
Halodimethylsulfonium halide 1, which is readily formed in situ from hydrohaloic acid and DMSO, is a good nucleophilic halide. This activated nucleophilic halide rapidly converts aryldiazonium salt prepared in situ by the same hydrohaloic acid and nitrite ion to aryl chlorides, bromides, or iodides in good yield. The combined action of nitrite ion and hydrohaloic acid in DMSO is required for the direct transformation of aromatic amines, which results in the production of aryl halides within 1 h. Substituted compounds with electron-donating or -withdrawing groups or sterically hindered aromatic amines are also smoothly transformed to the corresponding aromatic halides. The only observed by-product is the deaminated arene (usually 7%). The isolated aryldiazonium salts can also be converted to the corresponding aryl halides using 1. The present method offers a facile, one-step procedure for transforming aminoarenes to haloarenes and lacks the environmental pollutants that usually accompany the Sandmeyer reaction using copper halides.
Baik, Woonphil,Luan, Wanqiang,Lee, Hyun Joo,Yoon, Cheol Hun,Koo, Sangho,Kim, Byeong Hyo
p. 213 - 219
(2007/10/03)

Syntheses of 4-methoxymethylbenzyl permethrinates containing fluorine and their insecticidal activity
In order to investigate the relationship between the position of fluorine atom and insecticidal activity about 4-methoxymethylbenzyl permethrinates containing fluorine, 2 and 3-fluoro-4-methoxymethylbenzyl (±)-cis-permethrinate were synthesized. Their insecticidal activities were tested and the fluorine effect of title compounds was discussed.
Zou, Xinzhuo,Qiu, Zongxing
p. 173 - 179
(2007/10/03)

ipso Nitration. XXVII. The crystal structure and stereochemistry of 3-bromo-6-methyl-6-nitrocyclohexa-2,4-dienyl acetate, 5-bromo-2-methyl-6-nitrocyclohexa-2,4-dienyl acetate, and 3-bromo-6-methyl-6-nitrocyclohexa-2,4-dienyl chloride
The adduct obtained on nitration of 4-bromotoluene in acetic anhydride is (Z)-3-bromo-6-methyl-6-nitrocyclohexa-2,4-dienyl acetate.Its stereoselective rearrangement product, obtained on thermolysis in the presence of p-cresol, is (Z)-5-bromo-2-methyl-6-nitrocyclohexa-2,4-dienyl acetate.Reaction with hydrogen chloride in ether is also stereospecific and gives (Z)-3-bromo-6-methyl-6-nitrocyclohexa-2,4-dienyl chloride.The crystal structures of these compounds are reported.
Bushnell, Gordon W.,Fischer, Alfred,Henderson, George N.,Mahasay, Sumit Ray
p. 2382 - 2387
(2007/10/02)

ipso-Nitration: Formation of Nitronium Acetate Adducts in the Nitration of p-Acetamido-, p-Halogeno-, and p-Methoxy-toluenes, and α-p-Tolyloxyisobutyric acid
Low-temperature nitration of the title compounds in acetic anhydride gives 1,2-nitronium acetate adducts, except p-fluorotoluene which gives both 1,2 and 1,4 adducts and α-p-tolyloxyisobutyric acid which gives a spiro adduct.
Fischer, Alfred,Fyles, Deborah L.,Henderson, George N.
p. 513 - 514
(2007/10/02)