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(6-bromo-2, 3-difluorobenzyl) phenyl sulfide and preparation method thereof

A technology of difluorobenzyl and phenyl sulfide, which is applied in the field of (6-bromo-2,3-difluorobenzyl) phenyl sulfide and its preparation, can solve problems such as no literature reports, and achieve selection High performance, high yield, simple operation

Active Publication Date: 2019-05-24
ZHEJIANG UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] There is currently no literature report on (6-bromo-2,3-difluorobenzyl)phenyl sulfide and its synthesis method

Method used

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  • (6-bromo-2, 3-difluorobenzyl) phenyl sulfide and preparation method thereof
  • (6-bromo-2, 3-difluorobenzyl) phenyl sulfide and preparation method thereof
  • (6-bromo-2, 3-difluorobenzyl) phenyl sulfide and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: Preparation of (6-bromo-2,3-difluorobenzyl)phenylene sulfide

[0022] Add diphenyl disulfide (1.9 g, 8.75 mmol) into a 100 mL three-neck flask, replace argon three times at room temperature (empty the air), add 10 mL of tetrahydrofuran, add zinc (1.03 g, 15.85 mmol), and Sodium 2g, add water 16 mL. The temperature was raised to 70°C for reflux reaction. After the reflux solution turned from cloudy to clear, 1-bromo-2-(bromomethyl)-3,4-difluorobenzene (5.3 g, 17.6 mmol) was added and the reaction was continued for 4 hours. After the reaction was completed, ethyl acetate was added to the reaction solution for extraction, and the layers were separated into an organic phase and an aqueous phase. After the organic phase was washed with water and dried, the ethyl acetate solvent was concentrated under reduced pressure and spin-dried to obtain 3.46 g of a light yellow liquid. The yield is 60%. Melting point 34.2-36.8°C;

[0023] 1 H NMR (400 MHz, Chloroform-d) δ...

Embodiment 2

[0024] Example 2: Preparation of (6-bromo-2,3-difluorobenzyl)phenylene sulfide

[0025] Add diphenyl disulfide (1.9 g, 8.75 mmol) into a 100 mL three-necked flask, replace argon three times at room temperature (empty the air), add 10 mL of tetrahydrofuran, add sodium borohydride (0.60 g, 15.85 mmol), Sodium hydroxide 2g, add water 16mL. The temperature was raised to 70°C for reflux reaction. After the reflux solution turned from cloudy to clear, 1-bromo-2-(bromomethyl)-3,4-difluorobenzene (5.3 g, 17.6 mmol) was added and the reaction was continued for 4 hours. After the reaction was completed, ethyl acetate was added to the reaction solution for extraction, and the layers were separated into an organic phase and an aqueous phase. After the organic phase was washed with water and dried, the ethyl acetate solvent was concentrated under reduced pressure and spin-dried to obtain 5.59 g of a light yellow liquid. The yield is 95%. Melting point 34.2-36.8°C;

[0026] 1 H NMR (400...

Embodiment 3

[0027] Example 3: Preparation of (6-bromo-2,3-difluorobenzyl)phenylene sulfide

[0028] Add diphenyl disulfide (1.9 g, 8.75 mmol) into a 100 mL three-necked flask, replace argon three times at room temperature (empty the air), add 10 mL of tetrahydrofuran, add sodium borohydride (0.60 g, 15.85 mmol), Ammonia water 10mL. The temperature was raised to 70°C for reflux reaction. After the reflux solution turned from cloudy to clear, 1-bromo-2-(bromomethyl)-3,4-difluorobenzene (5.3g, 17.6 mmol) was added and the reaction was continued for 4 hours. After the reaction was completed, ethyl acetate was added to the reaction solution for extraction, and the layers were separated into an organic phase and an aqueous phase. After the organic phase was washed with water and dried, the ethyl acetate solvent was concentrated under reduced pressure and spin-dried to obtain 2.24 g of a light yellow liquid. The yield is 40%. Melting point 34.2-36.8°C;

[0029] 1 H NMR (400 MHz, Chloroform-d...

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Abstract

The invention discloses (6-bromine-2, 3-difluorobenzyl) phenyl sulfide and a preparation method thereof. The chemical structural formula of the (6-bromine-2, 3-difluorobenzyl) phenyl sulfide is shownin the description; the preparation method of the (6-bromine-2, 3-difluorobenzyl) phenyl sulfide comprises the following steps: using 6-bromine-2, 3 difluorobenzyl halogen and phenyl disulfide shown in the first formula as reaction raw materials, using preparing the (6-bromine-2, 3-difluorobenzyl) phenyl sulfide according to the first formula, using tetrahydrofuran as a solvent, carrying out nucleophilic substitution reaction under the action of a reducing agent and alkali, and synthesizing to obtain the (6-bromine-2, 3-difluorobenzyl) phenyl sulfide; in the first formula, X represents chlorine, bromine or iodine. The (6-bromine-2, 3-difluorobenzyl) phenyl sulfide has the advantages of high selectivity, high yield, simple operation and the like.

Description

technical field [0001] The invention relates to (6-bromo-2,3-difluorobenzyl)phenyl sulfide and a preparation method thereof. Background technique [0002] Influenza, the full name of influenza, is a disease caused by acute infection of the respiratory tract with highly contagious influenza virus. Its symptoms include fever, myalgia, listlessness and upper respiratory symptoms. [0003] Antiviral drugs can be used for the prevention and treatment of seasonal influenza, but they can only be strictly used as adjuvant drugs for vaccination, not as a substitute for vaccination. At present, drugs including M2 inhibitors (amantadine and rimantadine) and neuraminidase inhibitors (oseltamivir and zanamivir) are used for chemoprevention of influenza, and the effective rate is 70-90%. [0004] Baloxavir marboxil is an innovative Cap-dependent endonuclease inhibitor developed by Shionogi in Japan for the treatment of influenza A and influenza B. The advantage of this therapy is that i...

Claims

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Application Information

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IPC IPC(8): C07C323/07C07C319/14
Inventor 俞传明郑祥云卫禾耕陈俊宇姜昕鹏邵鸿鸣金逸中
Owner ZHEJIANG UNIV OF TECH
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