Method for preparing diaryl sulfone

A technology of diaryl sulfone and aryl sulfinate, applied to the preparation of organic compounds, chemical instruments and methods, formation/introduction of sulfonyl/sulfinyl groups, etc., to achieve mild reaction conditions and high reaction yield , easy to remove effect

Active Publication Date: 2014-03-19
ZHEJIANG ZHONGXIN FLUORIDE MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The problem that must be overcome is that the substrate needs to partially remove SO 2 After combining with another undesulfurized substrate, there is a requirement for high selectivity

Method used

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  • Method for preparing diaryl sulfone
  • Method for preparing diaryl sulfone
  • Method for preparing diaryl sulfone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Add 1 mmol of sodium p-tolylsulfinate and 0.5 mmol of copper chloride into a reaction tube filled with 2 ml of ethanol, heat to 50 degrees Celsius, and magnetically stir for 2 hours. After the reaction was completed, the solvent was spin-dried after cooling down to room temperature, and recrystallized to obtain the product with a yield of 96%.

[0036] Product Confirmation:

[0037]

[0038] 1 HNMR (400MHz, CDCl 3 ):δ7.81(d,J=7.6Hz,4H),7.20(d,J=7.6Hz,4H),2.39(s,6H); 13 C NMR (100MHz, CDCl 3 ): δ140.2, 139.9, 130.1, 129.8, 21.1; HRMS calcd for C 14 h 14 o 2 S:246.0715,found:246.0717.

Embodiment 2

[0040] Add 1 mmol of sodium p-dimethylaminophenyl sulfinate and 0.5 mmol of copper chloride into a reaction tube filled with 2 ml of ethanol, heat to 50 degrees Celsius, and stir magnetically for 2 hours. After the reaction was completed, the solvent was spin-dried after cooling down to room temperature, and the product was obtained by recrystallization with a yield of 90%.

[0041] Product Confirmation:

[0042]

[0043] 1 H NMR (400MHz, CDCl 3 ):δ7.83(d,J=8.8Hz,4H),7.25(d,J=8.8Hz,4H),3.09(s,12H); 13 C NMR (100MHz, CDCl 3 ): δ178.1, 159.1, 129.8, 123.0, 47.5. HRMS calcd for C 16 h 20 N 2 o 2 S:304.1245,found:304.1247.

Embodiment 3

[0045] Add 1 mmol of sodium p-cyanophenylsulfinate and 0.5 mmol of copper chloride into a reaction tube filled with 2 ml of ethanol, heat to 50 degrees Celsius, and stir magnetically for 2 hours. After the reaction was completed, the solvent was spin-dried after cooling down to room temperature, and the product was obtained by recrystallization with a yield of 93%.

[0046] Product Confirmation:

[0047]

[0048] 1 H NMR (400MHz, CDCl 3 ,TMS)δ7.58(d,J=7.2Hz,1H),7.51-7.54(m,3H),7.39-7.43(m,3H),7.30-7.37(m,2H).HRMS(EI)Calcd for C 12 h 9 Br(M + )231.9888, Found231.9887.

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PUM

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Abstract

The invention discloses a method for preparing diaryl sulfone and particularly relates to a copper chloride promoted method for preparing diaryl sulfone. The method is characterized by comprising the following step: taking aryl sulfinate as a raw material, carrying out a desulfurization coupling reaction on aryl sulfinate in an alcohol solvent under the action of copper chloride, so as to synthesize diaryl sulfone. According to the method, any ligand is not needed, inert gas shielding is not needed, and the diaryl sulfone of which the yield is 96 percent can be obtained.

Description

Technical field: [0001] The invention relates to a preparation method of diaryl sulfone, more specifically a preparation method of copper chloride-promoted diaryl sulfone. Background technique: [0002] As a medicine and pesticide intermediate, diaryl sulfone compound is often used in organic synthesis and shows 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 the Friedel-Crafts reaction of arylsulfonyl chlorides and arenes can only occur on the electron-rich aromatic ring and the substitution position is affected by the positioning effect of the substituent, which greatly limits the scope of applic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B45/04C07C317/14C07C317/36C07C317/44C07C315/00C07D213/71
Inventor 齐陈泽程凯陈寅镐袁其亮
Owner ZHEJIANG ZHONGXIN FLUORIDE MATERIALS CO LTD
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