Novel synthesis method of 4'-chloro-2-aminobiphenyl

A technology of aminobiphenyl and a new method, which is applied in the preparation of amino compounds from amines, organic chemistry, etc., and achieves the effect of simple treatment and high yield

Pending Publication Date: 2020-04-21
DEZHOU UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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  • Novel synthesis method of 4'-chloro-2-aminobiphenyl

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Experimental program
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Effect test

Embodiment 1

[0030] Put o-bromoaniline (1 mmol), p-chlorophenylboronic acid (1 mmol), sodium carbonate (1 mmol), palladium chloride (1 mol%) in a 25 mL round bottom flask, add water / ethanol (volume ratio 1: 1) Mixed solution 6 mL, 60 o C for 12 h. After the reaction was completed, it was cooled to room temperature, and then extracted with ethyl acetate. After spin-drying the organic solvent, the product was obtained by separation, and the yield was 60%.

Embodiment 2

[0032] Put o-bromoaniline (1 mmol), p-chlorophenylboronic acid (2 mmol), sodium carbonate (3 mmol), palladium acetate (2 mol%) in a 25 mL round bottom flask, add water / ethanol (volume ratio 1:1 ) mixed solution 6 mL, 100 o C under stirring for 24 h. After the reaction, it was cooled to room temperature, and then extracted with ether. After spin-drying the organic solvent, the product was obtained by separation with a yield of 97%.

Embodiment 3

[0034] Put o-bromoaniline (1 mmol), p-chlorophenylboronic acid (1.5 mmol), sodium carbonate (2 mmol), palladium acetate (1 mol%) in a 25 mL round bottom flask, add water / ethanol (volume ratio 1: 1) Mixed solution 6 mL, 80 o C under stirring for 24 h. After the reaction, it was cooled to room temperature, and then extracted with ether. After spin-drying the organic solvent, the product was obtained by separation with a yield of 93%.

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Abstract

The invention discloses a novel synthesis method of 4'-chloro-2-aminobiphenyl. O-bromoaniline and p-chlorophenylboronic acid are used as initial raw materials. The preparation method comprises the following steps: putting o-bromoaniline, 1-2 equivalents of p-chlorophenylboronic acid, 1-3 equivalents of alkali and 1-2 mol% of a palladium catalyst into a reactor, adding water or a water-organic solvent mixed solution as a reaction solvent into the reactor, and carrying out stirring at 60-100 DEG C for 12-24 hours, after the reaction is finished, cooling the product to the room temperature, and extracting the solution by using an organic solvent, carrying out spin-drying to remove the organic solvent, and carrying out separation to obtain the product. The method has the advantages that 1) o-bromoaniline with a low price is used as a starting material, 2) a simple palladium salt is used as a catalyst, and ligand participation is not needed, 3) the method can be carried out in air without inert gas protection, 4) the method can be completed in water or a water phase system in one step, 5) the method is simple in post-treatment and can achieve separation of a product and a reaction system through simple organic solvent extraction, and 6) the method is high in yield of 4'-chloro-2-aminobiphenyl.

Description

technical field [0001] The invention relates to the technical field of synthesis of pesticide intermediates, to a synthesis method of an agricultural fungicide intermediate, in particular to a synthesis method of the key intermediate 4'-chloro-2-aminobiphenyl of boscalid. Background technique [0002] Boscalid is a broad-spectrum, low-toxic, high-efficiency new type of nicotinamide systemic fungicide developed by BASF, which can effectively control powdery mildew, gray mold, sclerotinia, black spot, etc. A variety of diseases can be used for the prevention and treatment of related diseases including rapeseed, grapes, fruit trees, tomatoes, vegetables and field crops. Due to the limitation of the administrative protection period of boscalid, the large-scale production of boscalid in my country is only in its infancy, and the market potential is huge. [0003] 4'-Chloro-2-aminobiphenyl is the key intermediate of boscalid. According to the difference of raw materials, the met...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C209/68C07C211/52
CPCC07C209/68C07C211/52
Inventor 刘雷芳李文波王新芳
Owner DEZHOU UNIV
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