Method for synthesizing biphenylcarboxylic acid compound by using Suzuki coupling reaction

A coupling reaction, biphenyl carboxylic acid technology, applied in the field of organic chemical synthesis, can solve the problems of harsh reaction conditions, large catalyst dosage, low catalytic efficiency, etc., and achieves the effects of no high temperature treatment, low cost and high catalytic activity.

A coupling reaction, biphenyl carboxylic acid technology, applied in the field of organic chemical synthesis, can solve the problems of harsh reaction conditions, large catalyst dosage, low catalytic efficiency, etc., and achieves the effects of no high temperature treatment, low cost and high catalytic activity.

CN108484385AInactive Publication Date: 2018-09-04YICHUN UNIVERSITY
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  • Method for synthesizing biphenylcarboxylic acid compound by using Suzuki coupling reaction
  • Method for synthesizing biphenylcarboxylic acid compound by using Suzuki coupling reaction
  • Method for synthesizing biphenylcarboxylic acid compound by using Suzuki coupling reaction

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Embodiment Construction

[0021] The present invention utilizes Suzuki coupling reaction to synthesize the method for biphenyl carboxylic acid compound, uses brominated aromatic hydrocarbon and aryl boronic acid as raw material, uses water-soluble fullerene nano-palladium as catalyst, and described Suzuki coupling reaction equation is as follows:

[0022]

[0023] In the formula, R 1 , R 2 Represents the substituents at different positions, which can be electron-withdrawing or electron-donating substituents, or single or multiple substitutions, R 1 , R 2 Can be the same or different groups; the reaction conditions are as follows:

[0024] The molar ratio of bromoarene to arylboronic acid is 1.0:1.0-1.5; the reaction temperature is 0-75°C; the reaction time is 2-10h; the base used in the reaction is K 2 CO 3 、Na 2 CO 3 、Cs 2 CO 3 , KF, K 3 PO 4 any one or more of them. It is preferable to use K 2 CO 3 .

[0025] Below is the preparation method of the catalyst used in the present inventi...

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Abstract

The invention provides a method for synthesizing a biphenylcarboxylic acid compound by using the Suzuki coupling reaction. According to the method, brominated aromatic hydrocarbon and arylboronic acidare used as raw materials, and water-soluble fullerene nanopalladium is used as a catalyst; and the equation of the Suzuki coupling reaction is as described in the specification. In the equation, R1and R2 represent substituents at different positions, may be acceptor or donor substituents, and may be monosubstitutents or polysubstitutent; and R1 and R2 may be identical or different groups. The water-soluble fullerene nanopalladium catalyst is cheap, easily available and environmentally friendly, and has high catalytic activity and stable properties. When the catalyst is used for catalysis ofthe Suzuki coupling reaction, conditions are mild, anhydrous anaerobic treatment and high-temperature treatment are not needed, and cost is low. The method can be applied to the industrial synthesisof non-steroidal anti-inflammatory drugs such as diphenylacetic acid and diflunisal.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and relates to a method for synthesizing biphenyl carboxylic acid compounds through the Suzuki coupling reaction of brominated aromatic hydrocarbons and aryl boronic acid catalyzed by water-soluble fullerene nano-palladium, especially the synthesis of biphenyl carboxylic acid compounds by Suzuki coupling reaction. The method of benzene carboxylic acid compound. Background technique [0002] Biphenylcarboxylic acid compounds are common pharmaceutical intermediates, liquid crystal materials, polymer material monomers, and raw materials for treating certain diseases. They are widely used in the field of medicine and organic synthesis. The synthesis of such compounds usually goes through a series of aromatization reactions, diazotization reactions, Friedel-Crafts acylation reactions, Baeyer-Villiger rearrangement reactions, oxidative hydrolysis reactions, Kolbe-Schmitt reactions, etc., to fi...

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Application Information

Patent Timeline
04 Sep 2018
Publication
CN108484385A
IPC
C07C51/353; C07C63/331; C07C63/72; C07C65/24; C07C57/38; C07C57/58; B01J31/22
CPC
B01J31/2295; C07C51/353; C07C63/331; C07C63/72; C07C65/24; C07C57/38; C07C57/58
Inventors
刘万云; 霍平