Tetrahydrofuran → 1-[4-(1,1,2,2-Tetrafluoro-2-phenylethyl)phenyl]ethan-1-one

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Reaction Steps

A solution of 3.3 g. (0.0118 mole) of 4-(α,α,β,β-tetrafluorophenethyl)-benzonitrile in 25 ml. of dry, peroxidefree tetrahydrofuran is added dropwise to a stirred solution of about 0.03 mole of methylmagnesium bromide in 25 ml. of absolute ether in a nitrogen atmosphere. The mixture is stirred at reflux for about 26 hours. After cooling in an ice-bath, the adduct is hydrolyzed by the dropwise addition of about 5 ml. of water and the mixture is diluted with about 50 ml. of ether. The organic phase is decanted and the gelatinous precipitate is washed thoroughly with ether. The combined ethereal extracts are washed once with water, extracted with 15 ml. of ice-cold 6N hydrochloric acid in several portions, and then washed with water and dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure leaves the product as the oily solid residue. Sublimation at 95°-100°C. and 0.02 mm. gives purified material as white crystals, m.p. 128°-133°C. A sample for analysis, m.p. 134°-135.5 °C., is obtained by repeated recrystallization from hexane and resublimation.

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