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Method for synthesizing trifluorostyrene fluorine-containing monomer

A technology of trifluorostyrene and synthesis methods, applied in chemical instruments and methods, preparation of organic compounds, preparation of carbon-based compounds, etc., can solve the problems of low selectivity, low price, low yield, etc., and achieve easy availability of raw materials. , the effect of the simple method

Inactive Publication Date: 2011-11-16
SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

U.S. Patent No. 3,489,807 also prepares trifluorostyrene by cracking 3-chlorofluorophenylethane and 2-chloro-1,1-difluoroethylene at 600-800°C at high temperature, but the yield is lower
U.S.Patent No. 2,874, the method yield of synthetic trifluorostyrene with phenyllithium and tetrafluoroethylene reported in 166 is also low, and selectivity is not high
[0008] The reaction method of synthetic trifluorostyrene with relatively high yield was reported in (J.Org.Chem.1998,53,2714) by Heinze and Burton in 1998, but the raw material that these methods used is either trifluoroethylene or trifluoroethylene Bromofluoroethylene, but both raw materials are very expensive compared to chlorotrifluoroethylene

Method used

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  • Method for synthesizing trifluorostyrene fluorine-containing monomer
  • Method for synthesizing trifluorostyrene fluorine-containing monomer
  • Method for synthesizing trifluorostyrene fluorine-containing monomer

Examples

Experimental program
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Effect test

Embodiment 1

[0029] Example 1 Synthesis of 1,2,2-trifluorostyrene

[0030] Add phenylboronic acid (122mg), tetrakis(triphenyl)phosphine palladium (11.5mg), potassium phosphate (636mg) into the reaction tube with external condensing reflux jacket and branch pipe (without feeding sequence), add 2mL toluene solvent and appropriate amount After water, a dry ice reflux device was connected to the reaction tube to exchange argon. Fill the balloon with 5 times equivalent of chlorotrifluoroethylene and connect it to the branch tube of the reaction tube, then turn on the water in the outer condenser tube and then raise the temperature of the reaction tube to 95°C. After adding the dry ice acetone bath, open the branch valve, put in chlorotrifluoroethylene, keep the dry ice refluxed for 6 hours, and then pass the column with n-hexane to obtain a colorless liquid with a yield of 78%. 1 H NMR(300MHz, CDCl 3 ,293K,TMS)δ7.54-7.38(m,5H)ppm; 19 F NMR(282MHz, CDCl 3 , 293K, TMS)δ-100.12(dd, J=54.1, 25.1Hz, 1F...

Embodiment 2

[0031] Example 2 Synthesis of 1-methyl-2-(1,2,2-trifluorovinyl)benzene

[0032] Add o-toluene boronic acid (136mg), tetrakis(triphenyl)phosphine palladium (11.5mg), potassium phosphate (636mg) into the reaction tube with external reflux jacket and branch pipe (without feeding order), and add 2mL toluene After solvent and appropriate amount of water, a dry ice reflux device was connected to the reaction tube to exchange argon. Fill the balloon with 5 times equivalent of chlorotrifluoroethylene and connect it to the branch tube of the reaction tube, then turn on the water in the outer condenser tube and then raise the temperature of the reaction tube to 95°C. After adding the dry ice acetone bath, open the branch valve, put in chlorotrifluoroethylene, keep the dry ice refluxed for 6 hours, and then pass the column with n-hexane to obtain a colorless liquid with a yield of 77%. 1 H NMR(300MHz, CDCl 3 , 293K, TMS) δ 7.38-7.32 (m, 3H), 7.23-7.20 (m, 1H), 2.43 (s, 3H) ppm; 19 F NMR(282...

Embodiment 3

[0033] Example 3 Synthesis of 1-tert-butyl-4-(1,2,2-trifluorovinyl)benzene

[0034] Add 4-tert-butylphenylboronic acid (178mg), tetrakis(triphenyl)phosphine palladium (11.5mg), potassium phosphate (636mg) into the reaction tube with external reflux jacket and branch pipe (without feeding order), add After 2 mL of toluene solvent and an appropriate amount of water, a dry ice reflux device was connected to the reaction tube to exchange argon. Fill the balloon with 5 times equivalent of chlorotrifluoroethylene and connect it to the branch tube of the reaction tube, then turn on the water in the outer condenser tube and then raise the temperature of the reaction tube to 95°C. After adding the dry ice acetone bath, open the branch valve, put in chlorotrifluoroethylene, keep the dry ice refluxed for 6 hours, and then pass the column with n-hexane to obtain a colorless liquid with a yield of 85%. 1 H NMR(300MHz, CDCl 3 , 293K, TMS) δ7.53-7.46 (m, 4H), 1.40 (s, 9H) ppm; 19 F NMR(282MHz, ...

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Abstract

The invention relates to a method for synthesizing a trifluorostyrene fluorine-containing monomer. The monomer is obtained by making halogenated trichloroethylene react with ArBR under the catalytic actions of tetra(triphenylphosphine) palladium and potassium phosphate at reflux temperature. Raw materials are readily available, and the method is easy and convenient, and is a method suitable for industrial production.

Description

Technical field [0001] The invention relates to a method for synthesizing trifluorostyrene monomer. Background technique [0002] Today, when global strategic energy, especially the world's fossil energy resources, is increasingly valued, separating alternative new green and clean energy from civilian consumption has become one of the main goals of national energy reserves and new energy development in the "Twelfth Five-Year" energy plan. . [0003] Hydrogen energy has the advantages of being clean and inexhaustible, and it is called the mainstream energy in the 21st century. Proton exchange membrane fuel cell is an excellent device that uses hydrogen energy to generate electricity. It has a series of advantages such as low operating temperature, fast start-up, simple structure, good performance, long life and non-corrosive, so it is used in small and medium-sized mobile power sources, especially electric The car has great application value. Canadian Ballard Company has put its ...

Claims

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Application Information

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IPC IPC(8): C07B37/04C07C17/32C07C22/08C07C25/24C07C41/30C07C43/225C07C43/29
CPCC07C67/30C07C17/263C07C253/30C07C41/30C07B37/04C07C209/68C07C45/68C07C43/225C07C43/29C07C49/80C07C69/76C07C22/08C07C25/28C07C25/24C07C211/52C07C255/50
Inventor 陈盛沈其龙吕龙
Owner SHANGHAI INST OF ORGANIC CHEMISTRY - CHINESE ACAD OF SCI
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