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One-pot synthesis method for substituted diphenyl sulfide

A technology for diphenyl sulfide and diphenyl disulfide, which is applied to the field of one-pot synthesis of substituted diphenyl sulfide, can solve the problems of narrow application range of diphenyl sulfide, little industrial production, and high price, and achieves a reaction equipment Low requirements, avoid distillation process and the formation of high boilers, the effect of easy recovery

Inactive Publication Date: 2018-12-14
ZHEJIANG YANGFAN NEW MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0015] In this reaction route, the price of phenylboronic acid raw materials is relatively high, and the diphenyl sulfide obtained from the aromatic ring as the substrate is relatively narrow, and it cannot be used as a general method for industrial production.
[0016] In summary, although the methods for synthesizing substituted diphenyl sulfides are rich and diverse, considering factors such as the availability of raw materials, the price of catalysts, whether the reaction conditions are mild, whether the post-treatment is convenient, and the most important three wastes, few of them are truly effective. Applied to industrial production

Method used

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  • One-pot synthesis method for substituted diphenyl sulfide
  • One-pot synthesis method for substituted diphenyl sulfide
  • One-pot synthesis method for substituted diphenyl sulfide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036]Add 21.8g of diphenyl disulfide and 50mL of dichloroethane into the three-neck flask, cool down to 5-10°C, slowly add 13.4g of sulfuryl chloride dropwise, while controlling the internal temperature at 5-10°C, and the dropwise addition is completed in about 4 hours. Raise the temperature to 25-30°C to react for 2 hours, and remove 10 mL of dichloroethane under normal pressure. Cool in an ice bath to 5-10°C, add 31.9g of aluminum trichloride, keep stirring at this temperature for 1 hour, then slowly add 19.32g of toluene dropwise, the dropwise addition is completed in about 1 hour, and keep warm and separate for 3 hours after dropping. Slowly add the reaction solution into ice water to quench, extract the water phase with dichloroethane, combine the organic phases to recover the dichloroethane from the desolvation under reduced pressure, and collect the dichloroethane at 60-80pa under reduced pressure to collect the fraction at 90-95°C to obtain The color liqui...

Embodiment 2

[0038]

[0039] Add 21.8g of thiophenol and 50mL of dichloroethane into the three-neck flask, cool down to 5-10°C, slowly add 26.7g of sulfuryl chloride dropwise, while controlling the internal temperature at 5-10°C, and complete the dropwise addition in about 2 hours. Raise the temperature to 25-30°C to react for 2 hours, and remove 10-15 mL of dichloroethane under normal pressure. Cool in an ice bath to 5-10°C, add 31.6g of aluminum trichloride, keep stirring at this temperature for 1 hour, then slowly add 19.1g of toluene dropwise, the dropwise addition is completed in about 1 hour, and keep warm and separate for 3 hours after dropping. Slowly add the reaction solution into ice water to quench, extract the water phase with dichloroethane, combine the organic phases to recover the dichloroethane from the desolvation under reduced pressure, and collect the dichloroethane at 60-80pa under reduced pressure to collect the fraction at 90-95°C to obtain Color liquid 35.4g, yiel...

Embodiment 3

[0041]

[0042] Add 21.8g of diphenyl disulfide and 50mL of dichloroethane into the three-neck flask, cool down to 5-10°C, slowly add 13.4g of sulfuryl chloride dropwise, while controlling the internal temperature at 5-10°C, and the dropwise addition is completed in about 2 hours. Raise the temperature to 25-30°C to react for 2 hours, and remove 10-15 mL of dichloroethane under normal pressure. Cool in an ice bath to 5-10°C, add 31.9g of aluminum trichloride, keep stirring at this temperature for 1 hour, then slowly add 20.1g of fluorobenzene dropwise, the dropwise addition is completed in about 1 hour, and keep warm and separate for 3 hours after dropping. Slowly add the reaction solution into ice water to quench, extract the water phase with dichloroethane, combine the organic phases to recover the dichloroethane from desolvation under reduced pressure, and collect the dichloroethane at 60-80pa under reduced pressure to collect the fraction at 68-73°C to obtain The color ...

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Abstract

The invention relates to a one-pot synthesis method for substituted diphenyl sulfide. The process comprises the following steps: adding thiophenol or diphenyl disulfide and derivatives thereof into asolvent, dropwise adding sulfonyl chloride for a reaction so as to obtain a substituted benzene sulfuryl chloride solution, removing a part of the solvent at a normal pressure, adding Lewis acid, thendropwise adding substituted benzene for a Friedel-Crafts reaction, and carrying out distillation or recrystallization so as to obtain the substituted diphenyl sulfide. The method provided by the invention has the advantages of high safety, simple and convenient raw material recovery, greatly-reducedpurifying difficulty, easily-available raw materials, simple unit operation, low requirements on reaction equipment, mild reaction conditions, high yield and content and applicability to industrial production; and the content of the finally obtained substituted diphenyl sulfide product generally reaches 98% or more.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing substituted diphenyl sulfides in one pot. Background technique [0002] Diphenyl sulfide and its derivatives are an important class of fine chemical products, which are widely used in medicine, materials, pesticides and other fields. The synthetic method of this class compound mainly contains: [0003] 1. Patent CN104311463A discloses a method for preparing diphenyl sulfide: [0004] At high temperature, use sodium sulfide to react with chlorobenzene to obtain diphenyl sulfide. The reaction raw materials of this invention are easy to obtain, but the reaction conditions are relatively harsh, and the consumption of the reaction solvent is relatively large, so it can only be used to prepare diphenyl sulfide or symmetrical diphenyl sulfide. [0005] 2. Patent CN106946752A discloses a method for preparing diphenyl sulfide: [0006] Benzene and s...

Claims

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Application Information

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IPC IPC(8): C07C321/30C07C323/09C07C323/20C07C319/14C07C313/08
CPCC07C313/08C07C319/14C07C321/30C07C323/09C07C323/20
Inventor 汤文杰吴红辉杨清孙伟晔樊彬
Owner ZHEJIANG YANGFAN NEW MATERIALS
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