Method for preparing 4'-chloro-2-nitrobiphenyl

A technology of nitrobiphenyl and o-chloronitrobenzene, which is applied in the field of preparation of boscalid intermediate 4'-chloro-2-nitrobiphenyl, can solve the problem of low yield, many by-products and difficult separation And other problems, to achieve high yield, simple operation, good product quality effect

Inactive Publication Date: 2016-07-06
天津均凯农业科技有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] 1) Chinese patent CN201410711705.4 mentions that p-halophenylboronic acid or halogenated diphenylboronic acid and o-halogennitrobenzene react under heating conditions in a solvent to obtain 4'-chloro-2-nitrobiphenyl. In the reaction, only Select bromide or chloride; although the cost is low, the yield is also low at the same time, the reaction is easy to generate self-coupling products, and separation is difficult
[0005] 2) Goossen, LukasJ. et al. (Goossen, LukasJ. etal. Advanced Synthesis & Catalysis, 2009, 351 (16), 2667-2674; Goossen, LukasJ. etal. Chemistry-A European Journal. 2009, 15 (37), 9336-9349) studied A series of potassium o-nitrobenzoate and p-halochlorobenzene in cuprous iodide with a palladium compound as a catalyst, in N-m

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  • Method for preparing 4'-chloro-2-nitrobiphenyl

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Experimental program
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Effect test

Embodiment 1

[0027] 15.7g (0.1mol) o-chloronitrobenzene, 28.4g (0.13mol) potassium p-chlorotrifluorophenylborate, 27.6g (0.2mol) potassium carbonate, 16.1g (0.05mol) tetrabutylammonium bromide are added to In a three-necked flask, add 0.035g (0.00006mol) of cyclopalladium compound I, add 1240mL (69mol) of water (molar ratio: o-chloronitrobenzene: potassium p-chlorotrifluorophenyl borate: potassium carbonate: tetrabutyl bromide Ammonium chloride: cyclopalladium compound: water=1:1.3:2:0.5:0.0006:690); the temperature is raised to 100°C and the reaction is refluxed until the o-chloronitrobenzene reaction is complete. The reaction was stopped and cooled to room temperature. Filter, add 500mL dichloromethane to separate the filtrate, extract, and extract the aqueous phase twice with 500mL dichloromethane. Combine the organic phases, dry with anhydrous magnesium sulfate, filter, evaporate the filtrate and add 200mL petroleum ether to the remainder. Stir for 30 minutes, filter, and then recrysta...

Embodiment 2

[0029] 15.7g (0.1mol) o-chloronitrobenzene, 32.7g (0.15mol) potassium p-chlorotrifluorophenylborate, 30.4g (0.22mol) potassium carbonate, 25.7g (0.08mol) tetrabutylammonium bromide were added to In a three-necked flask, add 0.052g (0.00009mol) of cyclopalladium compound I, add 1310mL (73mol) of water (the molar ratio is: o-chloronitrobenzene: potassium p-chlorotrifluorophenyl borate: potassium carbonate: tetrabutyl bromide) Ammonium sulfide: cyclopalladium compound: water=1:1.5:2.2:0.8:0.0009:730); the temperature is raised to 95°C and the reaction is refluxed until the o-chloronitrobenzene reaction is complete. The reaction was stopped and cooled to room temperature. Filter, add 500mL dichloromethane to separate the filtrate, extract, and extract the aqueous phase twice with 500mL dichloromethane. Combine the organic phases, dry with anhydrous magnesium sulfate, filter, evaporate the filtrate and add 200mL petroleum ether to the remainder. Stir for 30 minutes, filter, and the...

Embodiment 3

[0031] 15.7g (0.1mol) o-chloronitrobenzene, 28.4g (0.13mol) potassium p-chlorotrifluorophenylborate, 26.2g (0.19mol) potassium carbonate, 19.3g (0.06mol) tetrabutylammonium bromide are added to In a three-neck flask, add 0.029g (0.00005mol) of cyclopalladium compound I, add 1280mL (71mol) of water (molar ratio: o-chloronitrobenzene: p-chlorotrifluorophenyl borate potassium: potassium carbonate: tetrabutyl bromide Ammonium chloride: cyclopalladium compound: water=1:1.3:1.9:0.6:0.0005:710); the temperature is raised to 100°C and the reaction is refluxed until the o-chloronitrobenzene reaction is complete. The reaction was stopped and cooled to room temperature. Filter, add 500mL dichloromethane to separate the filtrate, extract, and extract the aqueous phase twice with 500mL dichloromethane. Combine the organic phases, dry with anhydrous magnesium sulfate, filter, evaporate the filtrate and add 200mL petroleum ether to the remainder. Stir for 30 minutes, filter, and then recryst...

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Abstract

The invention provides a method for preparing 4'-chloro-2-nitrobiphenyl. The method comprises the following steps: o-chloronitrobenzene and p-chloro potassium benzyltrifluoroborate are adopted as raw materials which are added with a phase transfer catalyst and a palladium catalyst; and the 4'-chloro-2-nitrobiphenyl is obtained through reactions in an aqueous solution under a heating condition, wherein the reactions are carried out under a weak-base condition. The preparation method provided by the invention has the advantages of simplicity in operation, easily available raw materials, little environmental pollution, high yield, relatively good product quality and the like.

Description

Technical field [0001] The invention belongs to the technical field of preparation of chemical raw materials, and particularly relates to a preparation method of boscalid intermediate 4'-chloro-2-nitrobiphenyl. Background technique [0002] Chinese patent CN201310487320.X discloses that 4'-chloro-2-nitrobiphenyl is reduced to nitro group to obtain 4'-chloro-2-aminobiphenyl, and then reacted with 2-chloronicotinyl chloride to obtain the bactericide boscalid Bacteryl. Therefore, 4'-chloro-2-nitrobiphenyl is an important intermediate of the new nicotinamide fungicide boscalid, and the study of its preparation method is more important. [0003] The preparation method of 4'-chloro-2-nitrobiphenyl has the following reports: [0004] 1) Chinese patent CN201410711705.4 mentions that p-halophenylboronic acid or halogenated diphenylboronic acid and o-halonitrobenzene react under heating in a solvent to obtain 4'-chloro-2-nitrobiphenyl. Choose bromine or chlorinate; although the cost is low,...

Claims

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Application Information

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IPC IPC(8): C07C201/12C07C205/12C07D213/82B01J31/22C07F15/00
CPCC07C201/12B01J31/1805C07D213/82C07F15/006C07C205/12
Inventor 尚振华栗晓东
Owner 天津均凯农业科技有限公司
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