Method for continuously preparing 1-(methylsulfonyl)-2-(phenyl ethynyl) benzene by adopting electrochemical micro-channel

A technology of methylsulfonyl and phenylacetylene, applied in the direction of electrolytic components, electrolytic process, electrolytic organic production, etc., can solve the problems of using strong oxidant and long reaction process cycle

Active Publication Date: 2021-04-23
CHINA PHARM UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] Purpose of the invention: The technical problem to be solved by the present invention is to provide a method for continuously preparing 1-(methylsulfonyl)-2-(phenylethynyl)benzene by using an electroc...

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  • Method for continuously preparing 1-(methylsulfonyl)-2-(phenyl ethynyl) benzene by adopting electrochemical micro-channel
  • Method for continuously preparing 1-(methylsulfonyl)-2-(phenyl ethynyl) benzene by adopting electrochemical micro-channel
  • Method for continuously preparing 1-(methylsulfonyl)-2-(phenyl ethynyl) benzene by adopting electrochemical micro-channel

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Embodiment 1

[0039] Example 1 Synthesis of 1-(methylsulfonyl)-2-(phenylethynyl)benzene:

[0040] Dissolve 0.25 mmol (0.056 g) of compound 1 and 0.5 mmol of sodium acetate (0.041 g) in a mixed solution of 10 mL of ethanol and water (ethanol:water=4:1, that is, 8 mL of ethanol and 2 mL of water), The homogeneous solution A was obtained and added to the syringe pump a; the injection flow rate of the syringe pump a was 225 mL / min; the current was set to 10 mA, and the temperature was room temperature; the reaction volume of the microchannel reactor was V = 225 mL, and the reaction time was 1 min After a period of reaction in the microchannel reactor, the reaction liquid is collected, and the product yield calculated by HPLC is 90%, and the reaction liquid, after washing, drying and filtering, obtains the product 1-(formazan) after column chromatography separation sulfonyl)-2-(phenylethynyl)benzene. Such as image 3 with Figure 4 as shown, 1H NMR (400 MHz, DMSO- d 6 ) δ7.89 (dd, J = 7....

Embodiment 2

[0041] Example 2 Synthesis of 1-(methylsulfonyl)-2-(phenylethynyl)benzene:

[0042] Dissolve 0.25 mmol (0.056 g) of compound 1 and 0.5 mmol sodium acetate (0.041 g) in a mixed solution of 10 mL of acetonitrile and water (acetonitrile: water = 4:1, that is, 8 mL of acetonitrile and 2 mL of water), The homogeneous solution A was obtained and added to the syringe pump a; the injection flow rate of the syringe pump a was 225 mL / min; the current was set to 10 mA, and the temperature was room temperature; the reaction volume of the microchannel reactor was V = 225 mL, and the reaction time was 1 min After a period of reaction in the microchannel reactor, the reaction liquid was collected, and the product yield was calculated as 50% by the method of HPLC, and the reaction liquid was washed with water, dried, filtered, and obtained product 1-(formazol) after column chromatography separation sulfonyl)-2-(phenylethynyl)benzene.

Embodiment 3

[0043] Example 3 Synthesis of 1-(methylsulfonyl)-2-(phenylethynyl)benzene:

[0044] Dissolve 0.25 mmol (0.056 g) of compound 1 and 0.5 mmol sodium acetate (0.041 g) in a mixed solution of 10 mL of trifluoroethanol and water (trifluoroethanol:water=4:1, that is, 8 mL of trifluoroethanol and 2 mL of water) to obtain a homogeneous solution A, which was added to syringe pump a; the injection flow rate of syringe pump a was 225 mL / min; the current was set to 10 mA, and the temperature was room temperature; the microchannel reactor reaction volume V = 225 mL, reaction time 1 min; after a period of reaction in the microchannel reactor, the reaction liquid was collected, and the product yield was calculated by HPLC as 68%. The reaction liquid was washed with water, dried, filtered, and separated by column chromatography The product 1-(methylsulfonyl)-2-(phenylethynyl)benzene was obtained.

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Abstract

The invention discloses a method for continuously preparing 1-(methylsulfonyl)-2-(phenyl ethynyl) benzene by adopting an electrochemical micro-channel, which comprises the steps of dissolving methyl(2-(phenylethynyl) phenyl) thiane shown as a formula I in the description and an electrolyte in a solvent to obtain a homogeneous solution; and pumping the homogeneous solution into an electrochemical micro-channel reaction device, and carrying out an electrolytic reaction to obtain a reaction solution containing 1-(methylsulfonyl)-2-(phenyl ethynyl) benzene as shown in a formula II in the description. Compared with the prior art, the electrochemical micro-channel reaction device is adopted, the reaction time is short, the yield of reaction products is high, and the reaction efficiency is remarkably improved. Meanwhile, expensive metal catalysts or oxidizing agents do not need to be added, and the method is low in cost, easy and convenient to operate, environmentally friendly and green.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a method for continuously preparing 1-(methylsulfonyl)-2-(phenylethynyl)benzene by using an electrochemical microchannel reaction device. Background technique [0002] Sulfone is an important class of intermediates in organic synthesis, and has wide and good applications in the synthesis of chemistry, medicine, pesticides and materials science. For example, a variety of aryl sulfone compounds exhibit good pharmacological activities such as antifungal, antibacterial, anticancer, anti-AIDS, and anti-leprosy. In addition, aryl sulfones have also been found in COX-2 inhibitors The effect of the compound. Studies in recent years have also found that sulfones are also synthetic intermediates for a variety of new fuels. In addition, the sulfone functional group is easy to introduce and remove under mild conditions. The introduction of the sulfone group is conducive to th...

Claims

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Application Information

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IPC IPC(8): C25B3/07C25B3/23
Inventor 杨照刘莹沛方正林鑫鑫王志祥
Owner CHINA PHARM UNIV
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