704-35-8

Upstream product

• 79-38-9 Chlorotrifluoroethylene 
• 624-31-7 4-tolyl iodide 
• 598-73-2 1-bromo-1,2,2-trifluoroethene 
• 116-14-3 polytetrafluoroethylene 
• 4294-57-9 para-methylphenylmagnesium bromide 
• 446-65-1 2,2,2-trifluoro-1-(4-methylphenyl)ethanol 
• 102526-37-4 chloro(1,2,2-trifluoroethenyl)zinc 
• 2417-95-0 p-tolyllithium 

Downstream Products

• 67309-60-8 trans-p-methyl-α,α'-difluorostilbene 

Relevant academic research and scientific papers

Α, β, β-trifluorolactic of industrial manufacturing method (by machine translation)

PROBLEM TO BE SOLVED: To provide a method of producing industrially α,β,β-trifluorostyrenes. SOLUTION: The method of producing industrially the α,β,β-trifluorostyrenes includes a dehydrofluorination step of reacting α-aryl-α,β,β,β-tetrafluoroethanes with an alkali metal-bis(trimethylsilyl) amide, in the production of α,β,β-trifluorostyrenes, and an after-treatment step executed followed thereto to react a mixture containing the α,β,β-trifluorostyrenes of objective products and bis-(trimethylsilyl) amine of a byproduct with hydrogen fluoride, or a salt or a complex comprising an organic base and hydrogen fluoride. COPYRIGHT: (C)2012,JPO&INPIT

METHOD FOR PRODUCING SUBSTITUTED FLUORINE-CONTAINING OLEFIN

This invention relates to a method of reacting fluoroolefin with an organic magnesium compound in the presence of a catalyst comprising nickel or palladium so as to efficiently produce fluoroolefin, such as TFE, in which a fluorine (F) atom or atoms bonded to the sp2 hybridized carbon atom are substituted with an organic group.

Palladium-catalyzed coupling reactions of tetrafluoroethylene with arylzinc compounds

Organofluorine compounds are widely used in all aspects of the chemical industry. Although tetrafluoroethylene (TFE) is an example of an economical bulk organofluorine feedstock, the use of TFE is mostly limited to the production of poly(tetrafluoroethylene) and copolymers with other alkenes. Furthermore, no catalytic transformation of TFE that involves carbon-fluorine bond activation has been reported to date. We herein report the first example of a palladium-catalyzed coupling reaction of TFE with arylzinc reagents in the presence of lithium iodide, giving α,β,β-trifluorostyrene derivatives in excellent yields.

An efficient dehyrohalogenation method for the synthesis of α,β,β-trifluorostyrenes, α-chloro-β,β- difluorostyrenes and E-1-arylperfluoroalkenes

Dehydrofluorination of 1-aryl-1,2,2,2-tetrafluoroethanes (ArCHFCF 3) and 1-aryl-1-chloro-2,2,2-trifluoroethane (ArCHClCF3) using lithiumhexamethyldisilazide (LHMDS) in tetrahydrofuran (THF) at room temperature produced 1,2,2-trifluorostyrene and 1-chloro-2,2-difluorostyrene, respectively, in very good isolated yields. Dehydrofluorination of 1,2,2,3,3,3-hexafluoro-1-phenyl-propane (PhCHFCF2CF3) and 1,2,2,3,3,4,4,4-octafluoro-1-phenyl-butane (PhCHFCF2CF 2CF3) using LHMDS produced the corresponding substituted olefins (1-phenyl-1,2,3,3,3-pentafluoroprop-1-ene and 1-phenyl-1,2,3,3,4,4,4- pentafluorobut-1-ene) in good yield and high E-selectivity. Dehydrofluorination of 1-chloro-1-phenyl-2,2,3,3,3-pentafluoropropane (PhCHClCF2CF 3) and 1-chloro-1-phenyl-2,2,3,3,4,4,4-heptafluorobutane (PhCHClCF2CF2CF3) produced a mixture of the corresponding E and Z olefins (PhCClCFCF3 and PhCClCFCF 2CF3) in good yield.

A highly efficient room temperature non-organometallic route for the synthesis of α,β,β-trifluorostyrenes by dehydrohalogenation

Various 1-aryl-1,2,2,2-tetrafluoroethanes (ArCHFCF3, Ar=phenyl, substituted phenyl, naphthyl, heteroaryl) were synthesized by the fluorination of the corresponding alcohols with DAST. Dehydrofluorination of ArCHFCF3 using lithium hexamethyldisilazide (LHMDS) base in THF at room temperature produced 1,2,2-trifluorostyrenes (ArCF=CF2) in 61-91% isolated yields. This procedure provides an excellent non-organometallic alternative to the generally used metallation-Pd(0) coupling methods.

Solid-phase synthesis on functionalised fluoropolymer resins. Part 2: Preparation and properties of functional merrifieldtype resins possessing a perfluorinated polymer backbone

Monomers α,β,β-trifluorostyrene and 4-methyl-α,β,β- trifluorostyrene were prepared and were copolymerised under free-radical emulsion conditions to give highly stable, well defined lipophilic polymer resins. Benzylic halogenation of the polymer products gave 4-chloromethyl and 4-bromomethyl derivatives which could be elaborated through nucleophilic displacement of halide. The reaction of 4-fluorophenol with the 4- chloromethylated poly(trifluorostyrene) resin was followed by 1H and 19F NMR spectroscopy and proceeded more rapidly than for Merrifield resin. (C) 2000 Elsevier Science Ltd.

Reactivite des dienes et styrenes fluores obtenus par reaction de couplage au palladium

Fluorodienes and fluorostyrenes undergo clean cycloaddition to form perfluorocyclobutanes.Fluorostyrenes have been prepared by a palladium-catalyzed cross-coupling reaction.Treatment of fluorodienes under acidic conditions gives various α-fluorocarbonyl c