Electrochemical synthesis method of aryl sulfuric acid ester compound

A technology of aryl sulfinate and synthesis method, which is applied in the direction of electrolysis process, electrolysis components, electrolysis organic production, etc., to achieve the effects of wide substrate applicability, simple and safe operation, and mild conditions

Inactive Publication Date: 2018-12-07
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the defects of the existing synthetic route, the present invention provides an electrochemical synthesis method of aryl sulfinic acid ester compound, which has the advantages of simple process and convenient operation.

Method used

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  • Electrochemical synthesis method of aryl sulfuric acid ester compound
  • Electrochemical synthesis method of aryl sulfuric acid ester compound
  • Electrochemical synthesis method of aryl sulfuric acid ester compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028]

[0029] Add 4-chlorothiophenol (0.5mmol) and tetra-n-butyl ammonium tetrafluoroborate (0.3mmol) to a 25mL reaction tube equipped with a magnetic stirring bar, and then add 6.0mL methanol; fix the reaction tube on a magnetic stirring Add electrodes (graphite cathode, graphite anode) to conduct 20mA constant current electrolysis, and at the same time stir the reaction solution evenly; after the mixture reacts at room temperature (25°C) for 6h, the reaction ends; the solvent is removed with a rotary evaporator, and the crude product is passed through the column Chromatography (petroleum ether: ethyl acetate = 20:1) separation and purification gave the target product (2a) with a yield of 90%. The NMR data of this compound are: 1 H NMR (600MHz, CDCl 3 )δ7.63(d, J=8.6Hz, 2H), 7.50(d, J=8.5Hz, 2H), 3.46(s, 3H). 13 C NMR (101MHz, CDCl 3 )δ142.42, 138.73, 129.45, 126.96, 49.87.

Embodiment 2

[0031]

[0032] Add 4-bromothiophenol (0.5mmol) and tetra-n-butylammonium tetrafluoroborate (0.3mmol) to a 25mL reaction tube equipped with a magnetic stirrer, then add 6.0mL methanol; fix the reaction tube on a magnetic stirring Add electrodes (graphite cathode, graphite anode) to conduct 20mA constant current electrolysis, and at the same time stir the reaction solution evenly; after the mixture reacts at room temperature (25°C) for 6h, the reaction ends; the solvent is removed with a rotary evaporator, and the crude product is passed through the column Chromatography (petroleum ether: ethyl acetate = 20:1) separation and purification gave the target product (2b) with a yield of 86%. The NMR data of this compound are: 1 H NMR (600MHz, CDCl 3 )δ7.64(d, J=8.5Hz, 2H), 7.53(d, J=8.5Hz, 2H), 3.44(s, 3H). 13 C NMR (151MHz, CDCl 3 )δ142.74, 132.32, 127.12, 127.04, 49.94.

Embodiment 3

[0034]

[0035] Add 4-methylthiophenol (0.5mmol) and tetra-n-butylammonium tetrafluoroborate (0.3mmol) to a 25mL reaction tube equipped with a magnetic stirring bar, and then add 6.0mL methanol; fix the reaction tube on a magnetic On the stirrer, add electrodes (graphite cathode, graphite anode) to conduct 20mA constant current electrolysis, and at the same time stir the reaction solution evenly; after the mixture reacts at room temperature (25°C) for 6h, the reaction ends; the solvent is removed by a rotary evaporator, and the crude product is passed through The target product (2c) was obtained by separation and purification by column chromatography (petroleum ether: ethyl acetate = 20:1) with a yield of 76%. The NMR data of this compound are: 1 H NMR (600MHz, CDCl 3 )δ7.58(d, J=8.1Hz, 2H), 7.35–7.31(m, 2H), 3.46(s, 3H), 2.42(s, 3H). 13 C NMR (101MHz, CDCl 3 )δ142.91, 140.81, 129.75, 125.40, 49.46, 21.53.

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Abstract

The invention discloses an electrochemical synthesis method of an aryl sulfuric acid ester compound. Aryl sulfuric acid ester is subjected to green synthesis through constant-current electrolysis witharyl thiophenol and alcohol as raw materials in the existence of supporting electrolyte. The aryl sulfuric acid ester compound is synthesized through the electrochemical synthesis method without using a metal catalyst and an oxidizing agent, and the method has the characteristics of being high in atom economy, green, efficient, simple in process and the like and is suitable for industrial production.

Description

technical field [0001] The invention relates to an electrochemical synthesis method of an aryl sulfinate compound, belonging to the field of organic compound synthesis. Background technique [0002] Molecules containing sulfinate structures are an important class of organic compounds that exhibit a variety of biological and therapeutic activities, such as stimulating glucose uptake in muscle cells, regulating the mitochondrial function of Parkinson's disease protein DJ-1, etc. [1] . However, in the traditional sulfinate synthesis technology routes, excessive strong oxidizing agents, metal catalysts, etc. need to be used, which makes the reaction conditions harsh and limits the practicability of these methods. [2] . Therefore, the development of green and novel synthetic methods for aryl sulfinates has attracted extensive attention. The invention uses electrochemical synthesis technology, avoids the use of metal catalysts and strong oxidants, and the synthesis method has t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C25B3/02C25B3/23
CPCC25B3/23
Inventor 戴建军陶香长徐俊许华建
Owner HEFEI UNIV OF TECH
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