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Preparation method of aryl monothioether compound

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

Active Publication Date: 2020-09-08
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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  • Preparation method of aryl monothioether compound
  • Preparation method of aryl monothioether compound
  • Preparation method of aryl monothioether 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 monothioether compound. The method comprises the following steps: reacting halogenated hydrocarbon with an isopropyl magnesium halide Grignard reagent at -20 DEG C for 30 minutes until a halogen-magnesium exchange reaction is completely completed; cooling a reaction solution to -78 DEG C, slowly dropwise adding a tetrahydrofuran solution of asubstituted diphenyl disulfide compound into the newly prepared Grignard reagent, maintaining the concentration of the reactants to be 0.5-1 mmol / mL, carrying out a stirring reaction for 1 hour in anorganic solvent at -78 DEG C, and then slowly heating the reaction solution to room temperature; and carrying out a quenching reaction by using a saturated ammonium chloride solution, extracting an organic phase by using ethyl acetate or diethyl ether, drying the organic phase by using anhydrous magnesium sulfate, and concentrating the organic phase to obtain the aryl thioether compound. The method is simple in preparation process, low in cost, high in speed, easy to operate and small in environmental pollution, groups sensitive to Grignard reagents can also be tolerated, and high yield is 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 Applications(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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