Add time:07/14/2019         Source:sciencedirect.com

BrF3 reacts with monosubstituted phenyltrifluorosilanes X-C6H4SiF3 (X = H, p-Me, p-MeO, m-F, p-F, m-CF3, p-CF3) in equimolar reactions (CH2Cl2/MeCN solution, optimised reaction temperature) with three different patterns of products. Electron-rich aryl groups (X = H, p-Me, p-MeO) are only fluorinated, brominated and oxidised by BrF3. Monofluorinated phenyltrifluorosilanes behave mainly like the electron-rich silanes, but additionally, in smaller amounts, (ca. 1l0%) disubstitution takes place on BrF3 with formation of [(X-C6H4)2Br] [SiF5]. After methathesis the bromonium salts can be isolated as tetrafluoroborates or hexafluorophosphates. When X = m-CF3 and p-CF3, monosubstitution becomes as the main reaction and X-C6H4BrF2 can be isolated in good yields as first examples of hydrogen-containing phenylbromine difluorides. Their oxidation potential is high enough to oxidise 12 to IF5. Attempts to synthesise p- CF3C6H4BrCl2 were not successful.

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