Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

A kind of preparation method of halogenated alkanes synthesized with styrene and its derivatives and trichloroalkane

A technology of trichloroalkanes and halogenated alkanes, applied in the field of organic chemical synthesis, can solve the problems of low content, unfavorable drug discovery, difficult extraction and research, etc., to reduce emissions, ensure the health of operators, and make strong substrates universal sexual effect

Active Publication Date: 2021-03-02
WENZHOU UNIVERSITY
View PDF3 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, in the dimerization reaction of styrene and its derivatives, most of them are head-to-tail or head-to-head dimerization products. Even if there are tail-to-tail dimerization products in a few reactions, they are due to side reactions, and the content is very small. Difficult to extract and study, which is not conducive to drug discovery
However, there has not been a tail-to-tail dimerization product using styrene and its derivatives as reactants.

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • A kind of preparation method of halogenated alkanes synthesized with styrene and its derivatives and trichloroalkane
  • A kind of preparation method of halogenated alkanes synthesized with styrene and its derivatives and trichloroalkane
  • A kind of preparation method of halogenated alkanes synthesized with styrene and its derivatives and trichloroalkane

Examples

Experimental program
Comparison scheme
Effect test

specific Embodiment 1

[0029] Specific embodiment one: under visible light irradiation, the styrene of 0.2mmol, the trifluorotrichloroethane of 1.0mmol, the light redox catalyst fac-[Ir(ppy) of 0.006mmol 3 ], 2.0mmol of deionized water, 2.0mmol of triphenylphosphine, 1.0mmol of zinc iodide, and 1.0mmol of potassium phosphate were added to 2.0ml of tetrahydrofuran for reaction. Stir for 12 hours under a nitrogen atmosphere at a temperature of 25°C. After the reaction was over, hydrogen peroxide was added dropwise into the flask until the solution turned purple. Then, ethyl acetate was added to the mixture, washed with saturated sodium thiosulfate and brine. After extracting the aqueous layer with ethyl acetate, the combined organic layers were dried over anhydrous sodium sulfate and evaporated under vacuum. The residue was purified by flash column chromatography to give 32.8 mg of white solid 2,2,7,7-tetrachloro-1,1,1,8,8,8-hexafluoro-4,5-diphenyloctane, Yield 64%. m.p.122-124℃. 1 H NMR (500MHz,...

specific Embodiment 2

[0030] Specific embodiment two: under visible light irradiation, the 4-methylstyrene of 0.2mmol, the trifluorotrichloroethane of 1.0mmol, the photoredox catalyst fac-[Ir(ppy) of 0.006mmol 3 ], 2.0mmol of deionized water, 2.0mmol of triphenylphosphine, 1.0mmol of zinc iodide, and 1.0mmol of potassium phosphate were added to 2.0ml of tetrahydrofuran for reaction. Stir for 12 hours under a nitrogen atmosphere at a temperature of 25°C. After the reaction was over, hydrogen peroxide was added dropwise into the flask until the solution turned purple. Then, ethyl acetate was added to the mixture, washed with saturated sodium thiosulfate and brine. After extracting the aqueous layer with ethyl acetate, the combined organic layers were dried over anhydrous sodium sulfate and evaporated under vacuum. The residue was purified by flash column chromatography to give 29.7 mg of white solid 2,2,7,7-tetrachloro-1,1,1,8,8,8-hexafluoro-4,5-bis(4-methyl Phenyl)octane, 55% yield. m.p.84-86℃(u...

specific Embodiment 3

[0031] Specific embodiment three: under visible light irradiation, the 3-methylstyrene of 0.2mmol, the trifluorotrichloroethane of 1.0mmol, the photoredox catalyst fac-[Ir(ppy) of 0.006mmol 3 ], 2.0mmol of deionized water, 2.0mmol of triphenylphosphine, 1.0mmol of zinc iodide, and 1.0mmol of potassium phosphate were added to 2.0ml of tetrahydrofuran for reaction. Stir for 12 hours under a nitrogen atmosphere at a temperature of 25°C. After the reaction was over, hydrogen peroxide was added dropwise into the flask until the solution turned purple. Then, ethyl acetate was added to the mixture, washed with saturated sodium thiosulfate and brine. After extracting the aqueous layer with ethyl acetate, the combined organic layers were dried over anhydrous sodium sulfate and evaporated under vacuum. The residue was purified by flash column chromatography to give 36.2 mg of white solid 2,2,7,7-tetrachloro1,1,1,8,8,8 hexafluoro-4,5-bis(3-methylphenyl ) octane, yield 67%. m.p.75-77℃...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a halogenated alkane synthesized by using styrene and its derivatives and trichloroalkane and a preparation method thereof. By using styrene and its derivatives and trichloroalkane as substrates, chloroalkyl is carried out under light conditions. and dimerization reaction, reacting 10-14h to prepare trifluorodichloroalkane; wherein the reaction temperature is 10-45°C, and the reaction is carried out under normal pressure simultaneously; As a catalyst, the reaction speed is accelerated; at the same time, alkali, iodine source, triphenylphosphine and deionized water are added to the whole reaction system; the whole reaction is carried out in a solvent; meanwhile, the whole reaction needs to be carried out under a nitrogen atmosphere. After the reaction is completed, the halogenated alkane can be obtained after purification treatment, and the halogenated alkane is a tail-to-tail dimerization product prepared by using styrene and its derivatives as reactants. At the same time, the invention has the advantages of simple and easy-to-obtain raw materials, novel and simple preparation process, less pollution, low energy consumption and high yield.

Description

technical field [0001] The invention relates to the field of organic chemical synthesis, more specifically to a method for preparing halogenated alkanes synthesized from styrene and its derivatives and trichloroalkane. Background technique [0002] The introduction of halogen groups such as fluorine and chlorine into organic molecules has become a widely used drug discovery method, and the dimerization reaction of styrene and its derivatives has become one of the important reactions for introducing halogen groups. Or Lewis acid catalysis and transition metal catalysis have been used for this transformation. As we all know, even if two substances have the same chemical formula but different structural formulas, the two substances often have great differences in chemistry, physics and pharmacology. At present, in the dimerization reaction of styrene and its derivatives, most of them are head-to-tail or head-to-head dimerization products. Even if there are tail-to-tail dimeriz...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07C22/08C07C17/275C07C43/225C07C41/30C07C69/157C07C67/343C07C25/18C07C17/278C07C255/50C07C253/30C07B60/00
CPCC07B61/02C07B2200/03C07C22/08C07C25/18C07C43/225C07C69/157C07C255/50
Inventor 张兴国贺世瑜张小红叶寅璐黄叶鑫
Owner WENZHOU UNIVERSITY
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products