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Synthetic method of mercapto functionalized polyaryl carboxylic acid compound

A technology of aryl carboxylic acid and aryl fluoride, which is applied in the field of synthesis of mercapto-functionalized aryl carboxylic acid compounds, can solve the problems of long reaction cycle, insufficient universality, cumbersome operation, etc., shorten the reaction time, improve The effect of universality and simplified reaction conditions

Inactive Publication Date: 2015-03-25
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] Using the method described in formula 1 to synthesize mercapto-functionalized aryl carboxylic acid compounds, each step requires strict anaerobic conditions, complicated operation, long reaction cycle and low yield
Moreover, the method is limited by the raw materials, especially in the current situation where more thiol-functionalized aromatic carboxylic acid compounds need to be explored, and its universality is obviously not enough

Method used

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  • Synthetic method of mercapto functionalized polyaryl carboxylic acid compound
  • Synthetic method of mercapto functionalized polyaryl carboxylic acid compound
  • Synthetic method of mercapto functionalized polyaryl carboxylic acid compound

Examples

Experimental program
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Effect test

Embodiment 1

[0049] Example 1 2', 5'-dimercapto-p-terphenyl-4', 4'-dicarboxylic acid synthesis identification

[0050] (1) Synthesis and identification of 2',5'-difluoro-terphenyl-4',4'-dinitrile

[0051] The first is the traditional method (method 1), 1,4-difluoro-2,5-dibromobenzene (1089 mg, 4 mmol), 4-cyanophenylboronic acid (1293 mg, 8.8 mmol), potassium carbonate (2210 mg , 16 mmol) and a catalytic amount of palladium compound in a single-necked flask of 50 mL, under nitrogen protection, add 40 mL of deoxygenated toluene aqueous solution, reflux at 90 °C for 2 days, separate and purify by silica gel chromatography, and obtain a white powdery product (intermediate 1 ) 443 mg, yield 35%, ie intermediate 1.

[0052] This example uses the following method (method 2) to synthesize intermediate 1

[0053] In the new method of the present invention, 1,4-difluoro-2,5-dibromobenzene (1088 mg, 4 mmol), 4-cyanophenylboronic acid (1292 mg, 8.8 mmol), potassium carbonate (2208 mg, 16 m...

Embodiment 2

[0063] Example 2 Synthesis and identification of 2', 5'-dimercapto-p-terphenyl-4', 4'-dicarboxylic acid

[0064] The synthesis method is the same as in Example 1, the only difference is that when synthesizing intermediate 1, the organic solvent in the water / organic solvent mixed system used is polyethylene glycol 400, and the volume ratio of water and polyethylene glycol 400 is defined For factor E.

Embodiment 3

[0065] Example 3 Synthesis and identification of 2', 5'-dimercapto-p-terphenyl-4', 4'-dicarboxylic acid

[0066] The synthesis method is the same as in Example 1, the only difference is that when synthesizing intermediate 1, the organic solvent in the water / organic solvent mixed system used is polyethylene glycol 600, and the volume ratio of water and polyethylene glycol 600 is defined For factor F.

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Abstract

The invention relates to the technical field of compound synthesis and in particular discloses a synthetic method of a mercapto functionalized polyaryl carboxylic acid compound. The synthetic method concretely comprises the following steps: in the presence of a palladium catalyst, putting aryl fluoride, aryl boric acid and alkali metal salt serving as raw materials into a mixed system of water / organic solvent, and carrying out a series of subsequent reactions including Suzuki reaction to obtain the mercapto functionalized polyaryl carboxylic acid compound. According to the synthetic method disclosed by the invention, as the Suzuki reaction is realized in the air environment firstly, the reaction condition is greatly simplified, the reaction time is shortened from 2d to 1h, and the productivity and the yield are greatly increased; in addition, by adopting the environment-friendly solvent, the environment is beneficially protected; the mercapto functionalized polyaryl carboxylic acid compound synthesized by utilizing the synthetic method can be largely applied to metal organic compounds to build a series of novel porous materials with novel structures and excellent performances.

Description

technical field [0001] The invention relates to a new synthesis method of a compound containing a mercapto functional group, in particular to a new synthesis method of a mercapto functionalized aryl carboxylic acid compound. Background technique [0002] Mercapto compounds include mercaptans and thiophenols, which are important chemical raw materials and pharmaceutical intermediates. The sulfur contained in mercapto compounds involves a hybrid orbital composed of a larger 3s / 3p and a bond with a smaller 1s orbital of hydrogen, so The S-H bond is weak, making compounds containing thiol functional groups weakly acidic. The mercapto groups of mercapto compounds are easy to quickly complex with heavy metal ions such as mercury ions and silver ions, and form stable coordination compounds. Therefore, compounds containing thiol functional groups, on the one hand, can be used for the detoxification of heavy metal ions (Manuel Algarra a, María Isabel Vázquez. Chem. Eng. J. 2014, 253...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/62C07C319/02
Inventor 何军黄建吴超刘兴国黄家鸿曹鹏何永和
Owner GUANGDONG UNIV OF TECH
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