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Synthetic method of aryl-alkyl thioether compound

An aryl alkyl sulfide and a synthesis method technology, applied in the preparation of sulfide, organic chemistry and other directions, can solve the problems of limited application and high cost of aryl boronic acid substrates, achieve simple operation, no need for inert gas protection, and reaction conditions mild effect

Inactive Publication Date: 2014-05-21
中国人民解放军63975部队
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the high cost of aryl boronic acid substrates greatly limits its application

Method used

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  • Synthetic method of aryl-alkyl thioether compound
  • Synthetic method of aryl-alkyl thioether compound
  • Synthetic method of aryl-alkyl thioether compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1 takes sodium p-toluene sulfinate as raw material to synthesize 3-(p-tolylmercapto) methyl propionate:

[0021]

[0022] In a 10mL microwave reaction flask equipped with a magnet, add sodium p-toluenesulfinate (substrate 1a, 66.8mg, 0.36mmol), palladium chloride (10.6mg, 0.06mmol), silver carbonate (168.0mg, 0.6 mmol), solvent N,N-dimethylformamide / dimethyl sulfoxide (volume ratio 19 / 1, 2 mL), methyl 3-mercaptopropionate (substrate 2a, 38.04 μL, 0.3 mmol). Cover with a lid and stir at room temperature for 5 min. Then, react at 120° C. for 10 min under the heating power of 40 watts in a microwave reactor. TLC monitored the completion of the reaction. After the system was cooled to room temperature, it was filtered through a celite column and washed with dichloromethane. A small amount of silica gel was added, spin-dried, and flash column chromatography gave 15.8 mg of a colorless transparent liquid with a yield of 25%.

[0023] R f =0.44(V 正己烷 / V 乙酸...

Embodiment 2

[0024] Embodiment 2 takes sodium p-toluene sulfinate as raw material to synthesize 3-(p-tolylmercapto) methyl propionate:

[0025]

[0026] Operation method is the same as embodiment 1. The difference is that tetrahydrofuran (2 mL) was used instead of N,N-dimethylformamide and dimethyl sulfoxide as solvent, and 120W was used instead of 40W as microwave heating power. 44.1 mg of a colorless transparent liquid was obtained with a yield of 70%. Its R f , 1 H NMR, 13 C NMR, MS and other analytical data are the same as in Example 1.

Embodiment 3

[0028] Taking sodium p-toluene sulfinate as raw material to synthesize 3-(p-tolylmercapto) methyl propionate:

[0029]

[0030] Operation method is the same as embodiment 1. The difference is that 1,4-dioxane (2 mL) was used instead of N,A-dimethylformamide / dimethyl sulfoxide as solvent, and 180 W was used instead of 40 W as microwave heating power. 42.8 mg of a colorless transparent liquid was obtained with a yield of 68%. Its R f , 1 H NMR, 13 C NMR, MS and other analytical data are the same as in Example 1.

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Abstract

The invention relates to a synthetic method of aryl-alkyl thioether. According to the synthetic method, with aryl metal organic sulfinate (ArSO2M or (ArSO2)2M) as an arylation reagent and alkyl sulfhydryl as a reaction substrate, aryl-alkyl thioether is obtained under the actions of catalyzer and alkali. The aryl metal organic sulfinate is sodium salt, kali salt, lithium salt, silver salt, zinc salt and copper salt of aryl sulfinate. The aryl metal organic sulfinate is a arylation reagent with high efficiency and good universality.

Description

technical field [0001] The invention relates to a method for synthesizing aryl alkyl sulfide compounds. Background technique [0002] Arylalkylsulfide compounds and their oxidized derivatives are very important compounds, which are widely used in organic synthesis, medicine, bioactive molecules, pesticides, materials science and other fields. Especially in the field of medicine, aryl alkyl sulfide compounds and their oxidized derivatives occupy an important position, and some representative aryl alkyl sulfide skeleton structures are as follows: [0003] [0004] In the previous synthesis of diaryl sulfides or aryl alkyl sulfides, people often use expensive but relatively high activity brominated arenes and iodo arenes as coupling substrates, and some chlorinated arenes are also used as substrates and Coupling reactions of thiols or disulfides reported ((a) Kondo, T.; Mitsudo, T.-A. Chem. Rev. 2000, 100, 3205. (b) Hartwig, J.F.Acc.Chem.Res.2008 , 41, 1534. (c) Beletskaya...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C319/14C07C323/52C07C321/28
Inventor 肖军华李君臣王红梅
Owner 中国人民解放军63975部队
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