Dimethyl Sulfoxide → Benzene, 2-fluoro-4-(1-methylethenyl)-1-(trifluoromethyl)-

Participants

Reaction Conditions

Reaction Steps

To a suspension of 60% sodium hydride (1.96 g, 49.0 mmol) was added DMSO (40 ml) in one portion at 0° C. and the reaction mixture was heated at 80° C. for 40 minutes. After cooling to ambient temperature, to this was added a solution of methyltriphenylphosphonium bromide (17.5 g, 49.0 mmol) in anhydrous DMSO (50 ml) dropwise at 0° C. After being stirred for 1 hour at ambient temperature, to this was added a solution of 1-[3-fluoro-4-(trifluoromethyl)phenyl]ethanone (5.04 g, 24.5 mmol) in anhydrous DMSO (40 ml) dropwise at 0° C. and the reaction was stirred at ambient temperature for 1.5 hours. The mixture was quenched with water (150 ml) and extracted with hexane. The combined solution was washed with water then brine, dried over sodium sulfate and concentrated in vacuo to give the crude title compound (3.20 g containing hexane) as a yellow oil.

Provenance & Evidence