Method for preparing boscalid intermediate 2-(4-chlorophenyl) aniline

A boscalid and intermediate technology, which is applied in the field of preparation of boscalid intermediate 2-aniline, can solve the problems of harsh reaction conditions, complicated post-processing and high price, and achieves simple reaction, good product purity and high cost. low effect

Active Publication Date: 2015-04-22
JINGBO AGROCHEM TECH CO LTD
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  • Abstract
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Problems solved by technology

[0004] The purpose of the present invention is to provide a kind of synthetic process method suitable for industrialization, solve the traditional synthetic process of boscalid intermediate 2-(4-chlorophenyl) aniline raw material price is high, yield is low, post-processing complex, harsh reaction conditions To solve the problem, realize the simple reaction in the real sense, reduce the manufacturing cost, increase the content and yield

Method used

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  • Method for preparing boscalid intermediate 2-(4-chlorophenyl) aniline

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Experimental program
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Effect test

Embodiment 1

[0030] Room temperature, under nitrogen protection, add 45ml ethanol, 5.3g potassium hydroxide and 0.15mg KI, 15g (98%, 0.093mol) o-chloronitrobenzene, 15.3g (99%, 0.097mol) p-chlorobenzene to four-necked flask Boric acid, after stirring and dissolving evenly, add 0.75mg of Pd(PPh 3 ) 4 , and stirred to heat up to 75 ° C for 3 hours, the system was cooled to 40 ° C, filtered, and the filtrate was used;

[0031] Under nitrogen protection, add 0.45mg of Pd (PPh 3 ) 4 , adjust the temperature to 25°C and maintain a positive pressure of 0.01MPa to feed hydrogen for 4 hours;

[0032] Concentrate the reacted feed solution to 85°C, cool down, discharge, and suction filter to obtain a solid product while recovering the solvent to obtain 18.11 g of the product 2-(4-chlorophenyl)aniline with a content of 93.5% and a yield of 95.6%;

Embodiment 2

[0034] At room temperature, under nitrogen protection, add 60ml isopropanol, 5.58g sodium hydroxide and 0.45mg KI to the four-necked flask, add 15g (98%, 0.093mol) o-chloronitrobenzene, 14.69g (99%, 0.093mol) For p-chlorophenylboronic acid, stir and dissolve evenly, then add 1.2 mg of Pd / C, stir and heat up to 83°C for 3 hours, cool the system to 50°C and filter, and the filtrate is ready for use;

[0035] Under the protection of nitrogen, add 0.75mg of Pd / C to the above filtrate, adjust the temperature to 30°C, maintain a positive pressure of 0.03MPa, and pass in hydrogen for 4h;

[0036] After the reaction, the feed liquid was filtered and concentrated to 90 ° C, cooled, discharged, and suction filtered to obtain a solid product and recover the solvent at the same time to obtain 18.07 g of the product 2-(4-chlorophenyl) aniline with a content of 93.8% and a yield of 95.4 %;

Embodiment 3

[0038] At room temperature, under nitrogen protection, add 105ml tert-butanol, 12.52g potassium tert-butoxide and 0.30mg KI to the four-necked flask, add 15g (98%, 0.093mol) o-chloronitrobenzene, 15.3g (99%, 0.097mol ) p-chlorophenylboronic acid, stir and dissolve evenly, then add 15mg of Pd / molecular sieve, and stir to raise the temperature to 78°C for 5h, then cool the system to 45°C and filter, and the filtrate is ready for use;

[0039] Under the protection of nitrogen, add 0.45 mg of Pd / molecular sieve to the above filtrate, adjust the temperature to 27 ° C, maintain a positive pressure of 0.02 MPa, and pass in hydrogen for 4 hours;

[0040] Concentrate the reacted feed solution to 95° C., lower the temperature, discharge, and suction filter to obtain a solid product and recover the solvent at the same time to obtain 18.20 g of the product 2-(4-chlorophenyl)aniline with a content of 94.1% and a yield of 96.1%;

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Abstract

The invention belongs to the field of pesticides, relates to a technology for preparing agricultural fungicide intermediates and particularly relates to a technology for preparing boscalid intermediate 2-(4-chlorophenyl) aniline. The technology comprises the following steps of by adopting alcohol or formamide solvent, in an alkaline reagent and a KI system, under the action of Pd catalyst, carrying out Suzuki coupling reaction on o-chloronitrobenzene and p-chlorophenylboronic acid as raw materials to generate 2-(4-chlorophenyl)nitrobenzene, simply filtering the reaction system and directly carrying out catalytic hydrogenation on the reaction system to obtain the product. By the technology, the problems of high price of the raw materials, low yield, complex after-treatment and harsh reaction conditions of the traditional synthesis process of the boscalid intermediate are solved, the simple reaction is achieved in a true sense, the manufacturing cost is decreased, the content and yield of the product are increased and the technology is more conducive to industrial production.

Description

technical field [0001] The invention belongs to the technical field of pesticides, and relates to a preparation method of an agricultural fungicide intermediate, in particular to a preparation method of boscalid intermediate 2-(4-chlorophenyl)aniline. Background technique [0002] Boscalid, whose chemical name is 2-chloro-N-(4-chlorobiphenyl-2-yl) nicotinamide, is a new type of nicotinamide systemic fungicide developed by BASF, Germany. Inhibitors of succinate coenzyme Q reductase. It mainly controls many diseases such as powdery mildew, gray mold, sclerotinia, brown rot and root rot, and can be used to control crop-related diseases including rapeseed, grapes, fruit trees, tomatoes, vegetables and field crops. Its unique mechanism of action and no cross-resistance with other drugs make it an important new fungicide with huge market potential. In 2004, the countries where boscalid was registered for the first time in the world were the United Kingdom, Germany and Switzerlan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/52C07C209/36
Inventor 宫薇薇韦能春戴荣华曹同波王宗李洪侠
Owner JINGBO AGROCHEM TECH CO LTD
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