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A kind of preparation method of sulfoxide compound

A compound and sulfoxide technology, which is applied in the field of preparation of sulfoxide compounds, can solve the problems of difficult preparation of catalysts, poor reaction selectivity, harsh oxidation conditions, etc., and achieve the effects of low cost, mild conditions and high reaction efficiency

Active Publication Date: 2020-01-17
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the thioether oxidation systems reported today have defects such as harsh oxidation conditions, poor reaction selectivity, and difficult preparation of catalysts.
In particular, the extensive use of transition metal catalysts such as platinum, copper, and gold has brought serious environmental problems.

Method used

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  • A kind of preparation method of sulfoxide compound
  • A kind of preparation method of sulfoxide compound
  • A kind of preparation method of sulfoxide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Embodiment 1. Catalyzed synthesis of 1-bromo-4-(4-toluenesulfinyl)benzene by cercosporin catalyst

[0033] Add cercosporin (0.005mmol), p-bromobenzenetetrafluoroborate diazonium salt (0.5mmol), p-methylthiophenol (0.5mmol), 2mL chloroform, and 120 microliters of pyridine in sequence in a 10mL reaction tube, Then oxygen protection, 15W white light irradiation, room temperature 25 degrees Celsius reaction 24h. The reaction solution was washed three times with water, and the organic phase was collected and then dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated to dryness by rotary evaporation, and the thin-layer silica gel plate of 300-500 mesh was used for rapid separation, and the eluent used was ethyl acetate / petroleum ether (v:v=1:10) to obtain 1-bromo-4-(4 -toluenesulfinyl)benzene, yield 70%.

Embodiment 2

[0034] Embodiment 2. Catalyzed synthesis of 1-chloro-4-(4-toluenesulfinyl)benzene by cercosporin catalyst

[0035] Add cercosporin (0.005mmol), p-chlorobenzenetetrafluoroborate diazonium salt (0.5mmol), p-methylthiophenol (0.5mmol), 2mL chloroform, and 120 microliters of pyridine successively into a 10mL reaction tube, Then oxygen protection, 15W white light irradiation, room temperature 25 degrees Celsius reaction 24h. The reaction solution was washed three times with water, and the organic phase was collected and then dried over anhydrous magnesium sulfate. Filtrate, dry the solvent by rotary evaporation, and use a 300-500 mesh thin-layer silica gel plate to separate quickly, and the eluent used is ethyl acetate / petroleum ether (v:v=1:10) to obtain 1-chloro-4-(4 -toluenesulfinyl)benzene, yield 70%.

[0036] Embodiment 2. Catalyzed synthesis of 1-nitro-4-(4-toluenesulfinyl)benzene by cercosporin catalyst

[0037] Add cercosporin (0.005mmol), p-nitrobenzenetetrafluoroborate...

Embodiment 4

[0038] Embodiment 4. Catalyzed synthesis of 1-formaldehyde-4-(4-toluenesulfinyl)benzene by cercosporin catalyst

[0039] Add cercosporin (0.005mmol), p-formaldehyde benzenetetrafluoroborate diazonium salt (0.5mmol), p-methylthiophenol (0.5mmol), 2mL chloroform, and 120 microliters of pyridine in sequence in a 10mL reaction tube. Then oxygen protection, 15W white light irradiation, room temperature 25 degrees Celsius reaction 24h. The reaction solution was washed three times with water, and the organic phase was collected and then dried over anhydrous magnesium sulfate. Filtrate, dry the solvent by rotary evaporation, and use a 300-500 mesh thin-layer silica gel plate to separate quickly, and the eluent used is ethyl acetate / petroleum ether (v:v=1:10) to obtain 1-formaldehyde-4-(4 -toluenesulfinyl)benzene, yield 70%.

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Abstract

The invention discloses a preparation method for a sulfoxide compound and belongs to the technical field of catalysis. The invention provides a new green and environment-friendly method for efficiently synthesizing the sulfoxide compound. Under the action of catalyst, thiophenol, aryl diazonium compound and oxidizing agent are directly oxidized into the sulfoxide compound under the condition of light radiation, wherein cercosporin is served as the catalyst. According to the method disclosed by the invention, cercosporin is served as the catalyst; catalyzing condition is mild; catalysis can beperformed under room temperature and radiation of visible light; catalytic activity of catalyst is high; the catalyst can high-selectively catalyze synthesis of sulfoxide compound; with a trace amountof catalyst, yield can reach up to above 70%. The preparation method disclosed by the invention has the advantages of simple and easily acquired photocatalyst and substrate raw materials, environmental protection, low cost, large batch production and bright application prospect.

Description

technical field [0001] The invention belongs to the technical field of catalysis, and in particular relates to a preparation method of a sulfoxide compound. Background technique [0002] Sulfoxide compounds have important biological activities. By modifying the structure of sulfoxide compounds, their pharmacological activities can be improved, such as anti-ulcer, anti-virus, anti-HIV-1, anti-tumor, etc. In the field of pesticides, sulfoxide compounds have the advantages of less dosage and less pollution as fungicides and herbicides. Because the sulfoxide compound contains semi-polar groups, it is a kind of soft base neutral extractant, which has a special affinity for soft acid noble metals, so it has a high extraction rate and good selectivity for noble metals. At the same time, sulfoxide is an important part of many natural products and pharmaceutical intermediates. Therefore, it is of great significance to develop efficient and rapid methods for synthesizing sulfoxide, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/02C07C317/14C07C317/24C07C317/22
CPCC07C315/02C07C317/14C07C317/24C07C317/22
Inventor 饶义剑李佳张艳包文豪
Owner JIANGNAN UNIV
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