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A kind of method for synthesizing hexa(benzylthio)benzene

A technology of benzyl sulfide and hexaphenylthiophenol, applied in the field of organic synthesis, can solve the problems of restricting the industrialized production of compounds, restricting industrialized production, high price, etc., and achieves the effects of avoiding harsh reaction conditions, being suitable for industrialized production, and reducing production costs.

Inactive Publication Date: 2019-02-22
HENAN ACADEMY OF SCI CHEM RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Because this method uses strong alkali sodium hydride, so the synthetic process should control anhydrous anaerobic, limit the industrial production of this compound
And the used raw material hexachlorobenzene of this method is expensive on the market at present, is difficult to buy, also is a reason that restricts this compound suitability for industrialized production

Method used

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  • A kind of method for synthesizing hexa(benzylthio)benzene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Put 4.02g of hexathiophenol sodium salt, 10.26g of benzyl bromide, and 20mL of THF into a reaction flask, heat and react at 60°C for 4h, cool to room temperature after the reaction, add water and filter to obtain a yellow crude product. Washed twice with water and recrystallized from ethyl acetate to obtain 7.44 g of the product hexa(benzylthio)benzene. The purity by liquid phase detection was 98.3%, and the yield was 91.9%. 1 H NMR (400MHz, CDCl 3 ): δ (ppm) 7.20-7.28 (m, 30H), 4.09 (s, 12H); 13 C NMR (400MHz, CDCl 3 ) δ (ppm) 147.00, 137.38, 129.25, 128.39, 127.23, 42.44. MS (EI, m / z) 810.2.

Embodiment 2

[0016] Put 20.1g of hexathiophenol sodium salt, 51.3g of benzyl bromide, and 100mL of DMF into a reaction flask, heat and react at 50°C for 5h, cool to room temperature after the reaction, add water and filter to obtain a yellow crude product. Washed twice with water and recrystallized from ethyl acetate to obtain 34.72 g of the product hexa(benzylthio)benzene. The liquid phase detection purity was 98.5%, and the yield was 85.7%.

Embodiment 3

[0018] Put 20.1g of hexathiophenol sodium salt, 51.3g of benzyl bromide, and 100mL of diethyl ether into a reaction flask, heat and react at 35°C for 5h, cool to room temperature after the reaction, add water and filter to obtain a yellow crude product. Washed twice with water, and recrystallized from ethyl acetate to obtain 35.73 g of the product hexa(benzylthio)benzene. The liquid phase detection purity was 98.0%, and the yield was 88.2%.

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Abstract

The invention discloses a method for synthesizing hexakis(benzylthio)benzene and belongs to the field of organic synthesis. According to the method, hexa sodium thiophenolate and ebnzyl bromide are utilized as raw materials to directly react under existence of an organic solvent to generate the hexakis(benzylthio)benzene. Compared with the prior art, the method disclosed by the invention has a high yield (85 to 92%), the raw materials are easy to obtain, no dangerous catalyst is utilized, aftertreatment is simple, and the method is suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of organic synthesis and relates to a synthesis method of hexa(benzylthio)benzene. Background technique [0002] Hexa(benzylthio)benzene is an important organosulfur compound and a typical aromatic alkyl sulfide with good thermal stability, which can be used in the fields of organic light-emitting diodes and organic semiconductors. The synthesis of this compound was reported for the first time in 1989 (Z.Chem., 1989, 29). The synthesis method was the reaction of hexachlorobenzene and benzylmercaptan under the catalysis of sodium hydride in DMF at 10-15°C, with a yield of about 70%. Since the method uses strong alkali sodium hydride, the synthetic process must be controlled in anhydrous and oxygen-free manner, which limits the industrial production of the compound. And the used raw material hexachlorobenzene of this method is expensive on the market at present, is difficult to buy, is also a reason that restricts the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C319/14C07C321/28
CPCC07C319/14C07C321/28
Inventor 陈瑨刘长春霍萃萌赵永德代本才周洋
Owner HENAN ACADEMY OF SCI CHEM RES INST CO LTD