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Asymmetric diaryl sulfone compound and its preparation method

An asymmetric, diaryl technology, applied in the field of diaryl sulfone and its preparation, can solve problems such as not having practical value, and achieve the effects of high practicability and selectivity, mild conditions and low cost

Inactive Publication Date: 2016-08-17
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in previous literature reports, the copper-catalyzed synthesis of diaryl sulfones with potassium arylfluoroborates only had a yield of 28%. [6] , has no practical value

Method used

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  • Asymmetric diaryl sulfone compound and its preparation method
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  • Asymmetric diaryl sulfone compound and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Add 1 mmol of sodium p-methoxybenzenesulfinate, 1 mmol of potassium phenylfluoroborate, 1.2 mmol of sodium hydroxide and 0.1 mmol of cuprous chloride into a reaction tube containing 2 ml of dichloromethane, and stir magnetically for 3 hours. After the reaction is completed, filter through filter paper, spin dry the solvent, and separate by column to obtain the product. The yield was 95%.

[0035] 1-(4-Methoxyphenylsulfonyl)benzene Yellow solid(mp=90-92℃,lit mp88-90℃); 1 H NMR (300MHz, CDCl3) δ7.90 (m, 4H), 7.51 (m, 3H), 6.96 (m, 2H), 3.84 (s, 3H); HRMS calcd forC 13 h 12 o 3 S:248.0507,found:248.0509.

Embodiment 2

[0037] Add 1 mmol of sodium p-nitrobenzenesulfinate, 1 mmol of potassium phenylfluoroborate, 1.2 mmol of sodium hydroxide and 0.1 mmol of cuprous chloride into a reaction tube containing 2 ml of dichloromethane, and stir magnetically for 3 hours. After the reaction is completed, filter through filter paper, spin dry the solvent, and separate by column to obtain the product. The yield was 96%.

[0038] 1-(4-Nitrophenylsulfonyl)benzene Yellow solid(mp=145-149℃,lit mp143-145℃); 1 H NMR (400MHz, CDCl 3 ):δ8.27–8.38(m,2H),8.07–8.15(m,2H),7.92–8.00(m,2H),7.58–7.66(m,1H),7.51–7.61(m,2H).HRMS calcd for C 12 h 9 NO 4 S:263.0252,found:263.0250.

Embodiment 3

[0040] Add 1mmol of sodium benzenesulfinate, 1mmol of potassium p-bromophenylfluoroborate, 1.2mmol of sodium hydroxide and 0.1mmol of cuprous chloride into a reaction tube containing 2ml of dichloromethane, and stir magnetically for 3 hours. After the reaction is completed, filter through filter paper, spin dry the solvent, and separate by column to obtain the product. The yield was 94%.

[0041] 1-Bromo-4-(phenylsulfonyl)benzene Yellow solid (mp=100-101℃, lit mp98-99℃); 1 H NMR (400MHz, CDCl 3 ):δ7.88–7.99(m,2H),7.76–7.86(m,2H),7.61–7.69(m,2H),7.55–7.61(m,1H),7.46–7.52(m,2H).HRMS calcd for C 12 h 9 BrO 2 S:295.9507,found:295.9508.

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Abstract

The invention relates to an asymmetric diaryl sulfone compound and a preparation method thereof, and discloses diaryl sulfone into which aryl fluoborate catalyzed by cuprous chloride participates at room temperature, and a preparation method thereof. Available nontoxic aryl sulfinic acid sodium is selected as a substrate, and a low-cost reaction system is selected to develop coupling reaction of aryl sulfinic acid sodium and aryl potassium fluoborate catalyzed by cuprous chloride, so as to synthesize asymmetric diaryl sulfone. The diaryl sulfone synthesis method is economic and effective, mild in condition, short in reaction time, high in reaction yield and low in cost, and has good practicability and economic value.

Description

technical field [0001] The invention relates to a preparation method of an asymmetric diaryl sulfone compound, in particular to a diaryl sulfone catalyzed by cuprous chloride at room temperature and participated in by aryl fluoroborate and a preparation method thereof. Background technique [0002] As a medicine and pesticide intermediate, diaryl sulfone compounds are often used in organic synthesis and have shown good biological activity [1] , for example, diaryl sulfones have been shown to have antifungal, antibacterial, antitumor activities, etc. Recently, diaryl sulfones and aromatic heterocyclic sulfones have been shown to inhibit HIV-1 reverse transcriptase, representing a new class of substances that can solve the problems of drug residue toxicity and nucleoside inhibitor resistance. However, the preparation of diaryl sulfones by arylsulfonyl chlorides and arenes through the Friedel-Crafts reaction can only occur on the electron-rich aromatic ring and the substitutio...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/00C07C317/22C07C317/14
Inventor 朱余玲
Owner SHAOXING UNIVERSITY
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