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A kind of preparation method of aryl monosulfide compound

A technology for aryl monosulfides and compounds, which is applied in the field of preparation of synthetic aryl monosulfide compounds, can solve the problems of high requirements for reaction conditions, complex post-processing, and large environmental pollution, and achieve reduced production costs and high yields , the effect of reducing pollution

Active Publication Date: 2022-05-10
WUHAN INSTITUTE OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current synthesis methods of aryl monosulfide compounds use thiourea or substituted thiophenol as raw materials, the process is cumbersome, the reaction conditions are high, the post-treatment is complicated, and the environmental pollution is great.

Method used

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  • A kind of preparation method of aryl monosulfide compound
  • A kind of preparation method of aryl monosulfide compound
  • A kind of preparation method of aryl monosulfide compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1. Synthesis of Phenyl-p-Toluene Sulfide

[0042]

[0043] Add p-methyl bromide benzene (10mmol) and isopropylmagnesium chloride Grignard reagent (11mmol) to a pre-dried reaction flask filled with nitrogen (or argon), and react the mixture at -20°C for 30 minutes. The halo-magnesium exchange reaction was completely complete (reaction monitored by gas chromatography). Subsequently, the reaction solution was cooled to -78°C, and a solution of diphenyl disulfide (10 mmol) in tetrahydrofuran was slowly added dropwise to the newly prepared Grignard reagent, stirred and reacted at -78°C in an organic solvent for 1 hour, and then The reaction solution was slowly raised to room temperature. Quench the reaction with saturated ammonium chloride solution, extract the organic phase with ethyl acetate or ether, dry the organic phase with anhydrous magnesium sulfate, and concentrate the organic phase to obtain 1.6 g of a colorless oily liquid with a yield of 79% and a pu...

Embodiment 2

[0047] Example 2. Synthesis of phenyl p-methoxyphenyl sulfide

[0048]

[0049]Add p-methoxybromobenzene (10mmol) and isopropylmagnesium chloride Grignard reagent (11mmol) to a pre-dried reaction flask filled with nitrogen (or argon), and react the mixture at -20°C for 30 minutes. It completes the halo-magnesium exchange reaction completely (reaction monitored by gas chromatography). Subsequently, the reaction solution was cooled to -78°C, and a solution of diphenyl disulfide (10 mmol) in tetrahydrofuran was slowly added dropwise to the newly prepared Grignard reagent, stirred and reacted at -78°C in an organic solvent for 1 hour, and then The reaction solution was slowly raised to room temperature. Quench the reaction with saturated ammonium chloride solution, extract the organic phase with ethyl acetate or ether, dry the organic phase with anhydrous magnesium sulfate, and concentrate the organic phase to obtain 2.1 g of a colorless oily liquid with a yield of 95% and a ...

Embodiment 3

[0053] Example 3. Synthesis of 2,3-dihydro-5-benzofuran-p-methylphenylene sulfide

[0054]

[0055] Add 5-bromo-2,3-dihydrobenzofuran (10mmol) and isopropylmagnesium chloride Grignard reagent (11mmol) to a pre-dried reaction flask filled with nitrogen (or argon), and the mixture is kept at -20 °C for 30 minutes, until the halogen-magnesium exchange reaction is completely completed. Then the reaction solution was cooled to -78°C, and the tetrahydrofuran solution of p-methyldiphenyl disulfide compound (10 mmol) was slowly added dropwise to the newly prepared Grignard reagent, and the reaction was stirred at -78°C in an organic solvent After 1 hour, the reaction solution was slowly warmed to room temperature. Quench the reaction with saturated ammonium chloride solution, extract the organic phase with ethyl acetate or ether, dry the organic phase with anhydrous magnesium sulfate, and concentrate the organic phase to obtain a white solid 2,3-dihydro-5-benzofuran p-methyl Diph...

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Abstract

The invention discloses a preparation method of an aryl monosulfide compound. The steps include: reacting a halogenated hydrocarbon and an isopropylmagnesium halide Grignard reagent at -20°C for 30 minutes, and waiting for the halogen-magnesium exchange reaction to be completely completed . Then the reaction solution was cooled to -78°C, and the tetrahydrofuran solution of the substituted diphenyl disulfide compound was slowly added dropwise to the newly prepared Grignard reagent to maintain the concentration of the reactant at 0.5-1mmol / mL, in an organic solvent The reaction was stirred at -78°C for 1 hour, and then the reaction solution was slowly warmed to room temperature. Quench the reaction with saturated ammonium chloride solution, extract the organic phase with ethyl acetate or ether, dry the organic phase with anhydrous magnesium sulfate, and concentrate the organic phase to obtain the aryl sulfide compound. The method has the advantages of simple preparation process, low cost, high speed, easy operation, little environmental pollution, some groups sensitive to Grignard reagent can be tolerated, and higher yield can be obtained.

Description

technical field [0001] The present invention relates to a preparation method of aryl monosulfide compound, in particular to a method for synthesizing aryl monosulfide compound by using substituted diphenyl disulfide compound, isopropylmagnesium halide Grignard reagent and halogenated hydrocarbon as raw materials Preparation. Background technique [0002] Aryl monosulfide compounds (especially unsymmetrical diphenyl sulfide compounds) are an important class of pharmaceutical intermediates, widely used in medicine, pesticides, chemicals and other fields. The current synthesis methods of aryl monosulfide compounds use thiourea or substituted thiophenol as raw materials, which are cumbersome, require high reaction conditions, complicated post-treatment, and cause great environmental pollution. Contents of the invention [0003] Based on the above deficiencies in the prior art, the technical problem to be solved by the present invention is to provide a low-cost, environmentall...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/14C07C321/30C07C323/20C07D307/79C07B45/06
CPCC07C319/14C07D307/79C07B45/06C07C321/30C07C323/20
Inventor 董志兵王丹
Owner WUHAN INSTITUTE OF TECHNOLOGY
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