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Novel method for preparing 1-phenyl-2-benzene sulfonyl acetophenone

A technology of benzenesulfonyl ethyl ketone and bromoacetophenone, applied in the field of preparation of organic synthesis intermediates, can solve the problems of medium yield, high reaction temperature, and long reaction time

Inactive Publication Date: 2012-11-07
INNER MONGOLIA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of sulfone can be obtained by oxidation of thioether, or by the reaction of alkylating agent and sulfinate in a suitable polar solvent. Usually, the reaction temperature is high, the reaction time is long, and the yield is medium.

Method used

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  • Novel method for preparing 1-phenyl-2-benzene sulfonyl acetophenone
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  • Novel method for preparing 1-phenyl-2-benzene sulfonyl acetophenone

Examples

Experimental program
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Effect test

Embodiment 1

[0014] Example 1. Synthesis of 1-phenyl-2-benzenesulfonyl ethanone, the structural formula is as follows:

[0015]

[0016] Add 1.5mmol (246.2mg) of raw material sodium benzenesulfinate and 1.0mL of 50% ethanol aqueous solution into a 25ml round bottom flask, dissolve the raw materials under stirring conditions, and then add 1.0mmol (199.0) of 2-bromoacetophenone mg), and 0.2mmol (31.25mg) 1-butyl-3-methylimidazole hydroxide ([Bmim]OH) alkaline ionic liquid (structure: ) As a catalyst, the reaction is stirred at room temperature for 2 hours. After the completion of the reaction is detected by TLC, the reaction is stopped, and the crude product is obtained by suction filtration. The crude product was recrystallized with absolute ethanol to obtain 212.2 mg of pure white solid 1-phenyl-2-benzenesulfonyl ethanone with a purity of 98.6%. The isolated yield was 81.5% and the melting point was 93-94°C.

[0017] Identification of 1-phenyl-2-benzenesulfonyl ethyl ketone:

[0018] Infrared s...

Embodiment 2

[0022] In a 25ml round-bottom flask, add 1.2mmol (197.0mg) of raw material sodium benzenesulfinate and 1.0mL of 50% ethanol aqueous solution, dissolve the raw materials under stirring, and then add 1.0mmol (199.0) of 2-bromoacetophenone mg), and 0.2mmol (31.25mg) 1-butyl-3-methylimidazole hydroxide ([Bmim]OH) alkaline ionic liquid as a catalyst. The reaction was stirred at room temperature for 2 hours. After the reaction was completed by TLC, the reaction was stopped. reaction. Suction filtration to obtain a crude product. The crude product was recrystallized with absolute ethanol to obtain 204.6 mg of pure white solid 1-phenyl-2-benzenesulfonyl ethanone with a purity of 98.5%. The isolated yield was 78.6% and the melting point was 93-94°C.

[0023] The identification of the product is consistent with the literature report.

Embodiment 3

[0025] In a 25ml round-bottomed flask, 1.0mmol (164.16mg) of sodium benzenesulfinate as raw material and 1.0mL of 50% ethanol aqueous solution were added, and the raw materials were dissolved under stirring, and then 1.0mmol (199.0) of 2-bromoacetophenone was added. mg), and 0.2mmol (31.25mg) 1-butyl-3-methylimidazole hydroxide ([Bmim]OH) alkaline ionic liquid as a catalyst. The reaction was stirred at room temperature for 2 hours. After the reaction was completed by TLC, the reaction was stopped. reaction. Suction filtration to obtain a crude product. The crude product was recrystallized with absolute ethanol to obtain 177.8 mg of pure white solid 1-phenyl-2-benzenesulfonyl ethanone with a purity of 98.5%. The isolated yield was 68.3% and the melting point was 93-94°C.

[0026] The identification of the product is consistent with the literature report.

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Abstract

The invention relates to a novel method for preparing intermediate of organic synthesis 1-phenyl-2-benzene sulfonyl acetophenone. The invention uses alkaline ionic liquid 1-butyl-3-methyl imidazole hydroxide as a catalyst directly, and 1-phenyl-2-benzene sulfonyl acetophenone is prepared by one-step method through 2-bromo-acetophenone and sodium benzene sulfinate. The invention provides a novel method for preparing 1-phenyl-2-benzene sulfonyl acetophenone which has the advantages of short reaction time, mild condition, simple operation and high yield.

Description

Technical field [0001] The invention relates to a preparation method of organic synthesis intermediates, in particular to a preparation of 1-phenyl-2-benzenesulfonyl from 2-bromoacetophenone and sodium benzenesulfinate by using alkaline ionic liquid as a catalyst A new method of ethyl ketone. Background technique [0002] Sulfone is an important sulfur-containing organic synthesis intermediate, one of the research hotspots in organic sulfur, and has certain biological activity. The unique chemical properties of sulfone compounds include: sulfone can be used as an activated functional group to be introduced and removed freely under mild conditions; sulfone can activate α-position carbon atoms and act as a reaction center for the construction of CC bonds; the presence of sulfone groups Conducive to the passivation of intermediates and the formation of compound crystals, so the research on sulfones has received extensive attention. β-ketosulfone is one of the important sulfone com...

Claims

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Application Information

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IPC IPC(8): C07C317/24C07C315/00
Inventor 杜玉英田福利韩利民盛万里竺宁赵霜
Owner INNER MONGOLIA UNIV OF TECH
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