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Synthesis method of boscalid intermediate 2-(4 '-chlorphenyl) aniline

A synthetic method, the technology of boscalid, which is applied in the field of pesticide intermediate synthesis, can solve the problems of unsatisfactory yield, solid waste pollution, and high cost of p-chlorophenylboronic acid raw materials, and achieve low cost, simple operation, and high industrial efficiency. The effect on production value

Pending Publication Date: 2020-09-15
YINGDE GREATCHEM CHEM
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] It has been reported that the method of synthesizing boscalid intermediate 2-(4'-chlorophenyl)aniline is as follows: taking p-chlorophenylboronic acid and o-chloronitrobenzene as raw materials, in N,N-dimethylacetamide and water In the solution of palladium carbon as catalyst, potassium carbonate as cocatalyst, 2-(4'-chlorophenyl) nitrobenzene is obtained through Suzuki reaction; then in ethanol solution with zinc powder or iron powder as reducing agent, the reduction The key intermediate 2-(4'-chlorophenyl)aniline of the new fungicide boscalid was obtained. The raw material cost of p-chlorophenylboronic acid used in this method is high, and the solid waste pollution caused by zinc powder or iron powder reduction is serious
It is also reported that p-chloroaniline and aniline are used as raw materials, and p-chloroaniline generates diazonium salt under the action of sodium nitrite in water and hydrochloric acid, and then water, tetrahydrofuran or DMF and their mixed solvents are used as solvents. Gomberg-Bachmann reaction with aniline, although the process is simple, the yield is not very ideal

Method used

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  • Synthesis method of boscalid intermediate 2-(4 '-chlorphenyl) aniline
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  • Synthesis method of boscalid intermediate 2-(4 '-chlorphenyl) aniline

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Embodiment 1

[0048] Embodiment 1: the synthesis of 2-phenylbenzoic acid

[0049] The synthetic route of present embodiment 2-phenylbenzoic acid is as follows:

[0050]

[0051] Specifically: Add 18g (0.1mol) of 9-fluorenone, 42g (0.75mol) of potassium hydroxide and 300mL of toluene into the reaction flask, stir and heat up to 70°C, react for 12 hours, end the reaction, cool down to 25°C, add 500mL water, adjust the pH value to 1-2 with 36-38wt% hydrochloric acid, filter with suction, and dry to obtain the crude product of 2-phenylbenzoic acid with a yield of 96%.

Embodiment 2

[0052] Embodiment 2: the synthesis of 2-phenylbenzoic acid

[0053] The synthetic route of present embodiment 2-phenylbenzoic acid is the same as embodiment 1.

[0054] Specifically: add 33.6g (0.3mol) potassium tert-butoxide and 400mL tetrahydrofuran into the reaction flask, then add 18g (0.1mol) 9-fluorenone in batches, after the addition is complete, stir the reaction at 25°C for 1 hour, and monitor the completion of the reaction by HPLC Afterwards, concentrate to remove the organic solvent, add 500mL of water, adjust the pH value to 1-2 with 36-38wt% hydrochloric acid, filter with suction, and dry to obtain crude 2-phenylbenzoic acid with a yield of 99%.

Embodiment 3

[0055] Embodiment 3: the synthesis of 2-(4'-chlorophenyl) benzoic acid

[0056] The synthetic route of present embodiment 2-(4'-chlorophenyl) benzoic acid is as follows:

[0057]

[0058] Specifically: 10g (0.05mol) of 2-phenylbenzoic acid and 50mL of dichloroethane prepared in Example 1 or 2 were added to the reaction flask, the temperature was raised to 70°C, and 10.22g (0.75mol) was added dropwise within 2 hours. After the addition of sulfuryl chloride was completed, the reaction was carried out for 4 hours, and the solvent was recovered by distillation under reduced pressure to obtain the crude product of 2-(4'-chlorophenyl)benzoic acid with a yield of 95%.

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Abstract

The invention discloses a synthesis method of boscalid intermediate 2-(4 '-chlorphenyl) aniline, and belongs to the technical field of pesticide intermediate synthesis. The 2-(4 '-chlorphenyl) anilineis prepared by taking 9-fluorenone as an initial raw material through ring opening, chlorination, acylating chlorination, ammonification and Hofmann degradation reaction. The preparation method avoids the use of an expensive metal catalyst, the initial raw material is cheap and easy to obtain, and the method has the characteristics of simple reaction operation and high yield, and has higher valuein industrial production.

Description

technical field [0001] The invention belongs to the technical field of pesticide intermediate synthesis, and in particular relates to a synthesis method of boscalid intermediate 2-(4'-chlorophenyl)aniline. Background technique [0002] 2-(4’-Chlorophenyl)aniline is an important intermediate for the manufacture of boscalid. Boscalid is a new type of nicotinamide systemic fungicide developed by BASF in Germany. It is an inhibitor of succinate coenzyme Q reductase in the mitochondrial respiratory chain. It mainly controls powdery mildew, gray mold, sclerotinia and brown rot. It can be used to control crop-related diseases including rapeseed, grapes, fruit trees, tomatoes, vegetables and field crops. Its unique mechanism of action has no cross-resistance with other drugs, is safe for crops, and will not damage the ecology. It is 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 U...

Claims

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Application Information

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IPC IPC(8): C07C209/58C07C211/52C07C231/02C07C233/65C07C51/60C07C63/72C07C51/363C07C51/31C07C51/02C07C63/331
CPCC07C209/58C07C231/02C07C51/60C07C51/363C07C51/31C07C51/02
Inventor 王世银雷进海谭永清黄卫荣彭军陈锐东覃建海
Owner YINGDE GREATCHEM CHEM
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