Catalytic synthesis method of 2-substituted benzofuran compound

A technology of benzofuran and synthesis method, which is applied in the field of catalytic synthesis of 2-substituted benzofuran compounds, can solve the problems of high preparation cost and high price, and achieve the effects of low cost, increased yield, and high yield

Active Publication Date: 2019-05-10
ZHEJIANG WANLI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Using 2-alkynyl substituted phenols as raw materials, the synthesis of 2-substituted benzofuran compounds through intramolecular ring closure reaction is a relati...

Method used

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  • Catalytic synthesis method of 2-substituted benzofuran compound
  • Catalytic synthesis method of 2-substituted benzofuran compound
  • Catalytic synthesis method of 2-substituted benzofuran compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0010] Example 1: Under normal temperature and pressure, 10mmol of 2-(2-methyl)ethynylphenol was dissolved in 10mL of acetonitrile to obtain an acetonitrile solution of 2-(2-methyl)ethynylphenol; 0.5mmol cuprous chloride and 0.5mmol cesium carbonate; after that, stir at room temperature for 6 hours at a stirring rate of 600r / min, the reaction generates 2-methylbenzofuran, and 2-methylbenzofuran 1.2 is obtained by silica gel column chromatography g, its yield is 90.8%. Taking 2-(2-methyl)ethynylphenol as the reaction formula of raw material synthesis 2-methylbenzofuran in embodiment 1 is:

[0011]

[0012] According to calculations, in Example 1, the cost of the catalyst required to prepare 1 g of 2-methylbenzofuran is only 0.44 yuan, which is 2 orders of magnitude lower than the existing synthesis method using iridium catalyst as the catalyst.

Embodiment 2

[0013] Example 2: Under normal temperature and pressure, 20mmol 2-(2-ethyl)ethynylphenol was dissolved in 20mL acetonitrile to obtain an acetonitrile solution of 2-(2-ethyl)ethynylphenol; 1.0mmol cuprous chloride and 1.0mmol cesium carbonate; after that, stir at room temperature for 6 hours at a stirring rate of 500r / min, the reaction generates 2-ethylbenzofuran, and 2-ethylbenzofuran 2.8 is obtained by silica gel column chromatography g, its yield is 95.8%. Taking 2-(2-ethyl)ethynylphenol as the reaction formula of raw material synthesis 2-ethylbenzofuran in embodiment 2 is:

[0014]

[0015] According to calculations, in Example 2, the cost of the catalyst required to prepare 1 g of 2-ethylbenzofuran is only 0.37 yuan, which is 2 orders of magnitude lower than the existing synthesis method using iridium catalyst as the catalyst.

Embodiment 3

[0016] Example 3: Under normal temperature and pressure, 40mmol 2-(2-butyl)ethynylphenol was dissolved in 40mL of acetonitrile to obtain an acetonitrile solution of 2-(2-butyl)ethynylphenol; 2.0mmol cuprous chloride and 2.0mmol cesium carbonate; after that, stir at room temperature at a stirring rate of 800r / min for 6 hours, the reaction generates 2-butylbenzofuran, and 2-butylbenzofuran 6.4 is obtained by silica gel column chromatography g, its yield is 91.8%. Taking 2-(2-butyl) ethynylphenol as the reaction formula of raw material synthesis 2-butylbenzofuran in embodiment 3 is:

[0017]

[0018] According to calculations, in Example 3, the cost of the catalyst required to prepare 1 g of 2-butylbenzofuran is only 0.33 yuan, which is 2 orders of magnitude lower than the existing synthesis method using iridium catalyst as the catalyst.

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Abstract

The invention discloses a catalytic synthesis method of a 2-substituted benzofuran compound. The catalytic synthesis method includes the steps of dissolving 2-alkynyl substituted phenol in acetonitrile under normal temperature and normal pressure to obtain an acetonitrile solution of the 2-alkynyl substituted phenol, wherein the molar volume ratio of the 2-alkynyl substituted phenol to the acetonitrile is 1:1mmol/mL; adding cuprous chloride and cesium carbonate to the acetonitrile solution, wherein the molar ratio of each of the cuprous chloride and the cesium carbonate is 5% of that of the 2-alkynyl substituted phenol; stirring the solution at room temperature for 6 hours to generate the 2-substituted benzofuran compound after reaction. The catalytic synthesis method of the 2-substitutedbenzofuran compound has low cost and high yield; the cost of a catalyst required for preparing 1g of the 2-substituted benzofuran compound is reduced by two orders of magnitude as compared with that of existing synthesis methods in which iridium catalysts are used, and the yield is increased to 88.5 to 95.8%.

Description

technical field [0001] The invention relates to a compound synthesis method, in particular to a catalytic synthesis method of 2-substituted benzofuran compounds. Background technique [0002] 2-Substituted benzofuran compounds widely exist in natural products and pharmaceutical molecules, and have attracted much attention because of their good antibacterial, antioxidant, and antiviral activities. Using 2-alkynyl substituted phenols as raw materials, the synthesis of 2-substituted benzofuran compounds through intramolecular ring closure reaction is a relatively common preparation method, but expensive noble metal catalysts, equivalent Alkali or higher temperature, its preparation cost is higher, and product yield is moderate. As reported in the literature, the noble metal iridium catalyst can convert 2-(2-phenyl)ethynylphenol into 2-phenylbenzofuran at 110° C. with toluene as a solvent, with a yield of 72%. According to the market price of the iridium catalyst, the cost of ...

Claims

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Application Information

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IPC IPC(8): C07D307/36
Inventor 戎舟挺钱国英
Owner ZHEJIANG WANLI UNIV
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