74298-22-9Relevant articles and documents
Three-step regioselective synthesis of 2,3-difluorohalobenzenes using tetrafluoroethylene and buta-1,3-diene as starting building blocks
Egorov, M. P.,Lipkind, M. B.,Nefedov, O. M.,Volchkov, N. V.
, p. 925 - 932 (2021/06/07)
The gas-phase copyrolysis of tetrafluoroethylene and buta-1,3-diene in a flow tube reactor at 490–510 °C gives 3,3,4,4-tetrafluorocyclohex-1-ene, which is selectively converted to 1-bromo- or 1-chloro-2,3-difluorobenzene via intermediate steps of halogenation and dehydrohalogenation.
New Method for Selective Monofluorination of Aromatics Using Silver Difluoride
Zweig, Arnold,Fischer, Robert G.,Lancaster, John E.
, p. 3597 - 3603 (2007/10/02)
Fluorobenzene is obtained in 61percent yield from reaction of a solution of benzene in n-hexane with solid argentic fluoride (AgF2).The AgF2 acts as both a strong oxidant and the fluoride source.Cobaltic fluoride provides only low (8percent) yields of fluorobenzene under similar conditions.The predominant reaction of benzene solutions with AgF2 appears to proceed by a process involving initial electrophilic oxidative cis addition of two fluorine atoms from the solid AgF2 lattice to the para aromatic positions, leading to cis-3,6-difluoro-1,4-cyclohexadiene (F2CHD).The reductive elimination leaves solid argentous fluoride (AgF) which is easily recoverable by filtration.Elimination of HF from the F2CHD yields fluorobenzene.Reactions of haloaromatics with AgF2 generally proceed in a similar manner.Thus, further reaction of AgF2 with benzene or monohalo- or p-dihalobenzenes leads in steps to 3,3,6,6-tetrafluoro-1,4-cyclohexadiene (F4CHD) in up to 82percent yield.The modest to high yields of mono- and specific polyfluorinated aromatics contrast sharply with reported nonselective perfluorination in vapor-phase reactions of aromatics over AgF2 or CoF3.Reactions of AgF2 or CoF3 with solutions of nitrobenzene, acetophenone, benzoic acid, and benzonitrile give mixtures of o-, m-, and p-monofluoro derivatives.
