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Method for synthesizing (E)-(2-(phenylsulfonyl)vinyl)benzene and derivative thereof

A technology of benzenesulfonyl and derivatives, applied in the field of synthesis-vinyl)benzene and derivatives thereof, can solve the problems of low yield, high cost, harsh reaction conditions, etc., and achieves cost reduction, yield improvement, and reaction conditions. mild effect

Inactive Publication Date: 2018-06-22
HUNAN AGRICULTURAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The technical problem solved by the present invention is that there are harsh reaction conditions in the existing method for synthesizing (E)-(2-(phenylsulfonyl)vinyl)benzene or (E)-(2-(acyl)vinyl)benzene derivatives, Low yield, high cost

Method used

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  • Method for synthesizing (E)-(2-(phenylsulfonyl)vinyl)benzene and derivative thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Synthesis of (E)-(2-(phenylsulfonyl)vinyl)benzene

[0028] The substrate 31.2mg (0.3mmol) styrene, sodium benzene sulfinate 98.4mg (0.6mmol), the catalyst 5.1mg (0.03mmol) AgNO 3 , Oxidant 137.0mg (0.6mmol) (NH 4 ) 2 S 2 O 8 , TEMPO 5.4mg (0.06mmol). Add 1 mL of solvent toluene into a 25 mL sealed tube under air. Then put the sealed tube in an oil bath at 100°C for 2h. After the reaction, the reaction solution was cooled to room temperature. Add 40 mL of saturated brine, extract three times with 100 mL of ethyl acetate, and combine the organic layers. The organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure and separated by silica gel column chromatography (ethyl acetate / petroleum ether: 1 / 8 as eluent) to obtain 51.3 mg of yellow liquid with a yield of 89%.

Embodiment 2

[0029] Example 2: Synthesis of (E)-1-chloro-4-(2-(benzenesulfonyl)vinyl)benzene

[0030] The substrate 41.6mg (0.3mmol) p-chlorostyrene, sodium benzenesulfinate 98.4mg (0.6mmol, catalyst 5.1mg (0.03mmol) AgNO 3 , Oxidant 137.0mg (0.6mmol) (NH 4 ) 2 S 2 O 8 TEMPO 5.4 mg (0.06 mmol). 1 mL of solvent toluene was added to a 25 mL sealed tube under air. Then put the sealed tube in an oil bath at 100°C for 2h. After the reaction, the reaction solution was cooled to room temperature. Add 40 mL of saturated brine, extract three times with 100 mL of ethyl acetate, and combine the organic layers. The organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure and separated by silica gel column chromatography (ethyl acetate / petroleum ether: 1 / 8 as eluent) to obtain 63.5 mg, with a yield of 86%.

[0031] 1 H NMR (400MHz, CDCl3) δ 7.86 (d, J = 7.7 Hz, 2H), 7.56 (d, J = 15.4 Hz, 1H), 7.55 (d, J = 8.6 Hz, 1H), 7.49 (t, J =7.7Hz, 2H), 7...

Embodiment 3

[0034] Example 3: Synthesis of (E)-2-chloro-4-(2-(benzenesulfonyl)vinyl)benzene

[0035] The substrate 41.6mg (0.3mmol) o-chlorostyrene, sodium benzenesulfinate 98.4mg (0.6mmol), the catalyst 5.1mg (0.03mmol) AgNO 3 , Oxidant 137mg (0.6mmol) (NH 4 ) 2 S 2 O 8 , TEMPO 5.4mg (0.06moml). 1mL of solvent toluene was added to 25mL sealed tube under air. Then put the sealed tube in an oil bath at 100°C for 2h. After the reaction, the reaction liquid was cooled to room temperature. Add 40 mL of saturated brine, extract three times with 100 mL of ethyl acetate, and combine the organic layers. The organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was distilled under reduced pressure and separated by silica gel column chromatography (ethyl acetate / petroleum ether: 1 / 8 as eluent) to obtain 67.7 mg, with a yield of 81%.

[0036] 1 H NMR(400MHz, CDCl 3 )δ8.02(d,J=15.4Hz,1H),7.90(d,J=8.0Hz,2H),7.57(t,J=7.3Hz,1H),7.50(t,J=7.7Hz,2H) ,7.44(d,J=7.7Hz,1H), 7.36(d,J=8...

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Abstract

The invention provides a method for synthesizing (E)-(2-(phenylsulfonyl)vinyl)benzene and a derivative thereof. The method adopts styrene or a derivative of styrene as a reactant A and sodium benzenesulfinate or a derivative of sodium benzenesulfinate as a reactant B, and the reactant A and the reactant B react under the oxidation of persulphate to generate (E)-(2-(acyl)vinyl)benzene and the derivative thereof. Compared with the conventional method utilizing thioether oxidation, sulfur dioxide addition, Friedel-Crafts sulfonylation and transition metal catalysis coupling, the method increasesyield, and since the method utilizes relatively cheap persulphate as oxidant to carry out reaction, the cost of synthesis is reduced.

Description

Technical field [0001] The present invention relates to a method for synthesizing (E)-(2-(benzenesulfonyl)vinyl)benzene and its derivatives. Background technique [0002] (E)-(2-(phenylsulfonyl)vinyl)benzene, English name: (E)-(2-(phenylsulfonyl)vinyl)benzene, chemical structure: Molecular formula: C 14 H 12 O 2 S; Molecular weight: 244.31. [0003] Sulfone is an important organic synthesis intermediate, which has a wide range of applications in chemistry, medicine, pesticide and material science synthesis, and has certain biological activities. The synthesis of traditional vinyl sulfone usually involves sulfide oxidation, sulfur dioxide addition, Friedel-Crafts sulfonylation and transition metal catalyzed coupling. Vinyl sulfone is an intermediate for many new dyes. The sulfone functional group is easy to introduce and remove under mild conditions. The introduction of the sulfone group can activate the α-position carbon atom and make it react with acid and various electrophiles...

Claims

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Application Information

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IPC IPC(8): C07C315/00C07C317/14
Inventor 桂清文蒋红梅刘晓颖韩康赵文魁
Owner HUNAN AGRICULTURAL UNIV
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