Water → 2-(3,5-Dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfide

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Reaction Conditions

Reaction Steps

Triphenyl[(phenylsulfanyl)methyl]phosphonium chloride (50.0 g, 116 mmol) and potassium carbonate (32.2 g, purity 98%, 233 mmol) were suspended in toluene (1 L) under an inert gas atmosphere (argon) and cooled to 5° C. 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanone (29.5 g, purity 96%, 116 mmol) and polyethyleneglycole (MW 1500, 8.76 g, 5.82 mmol) were added and the reaction mixture was stirred for five and a half hours at 5° C. and after warming to room temperature stirred for additional two hours. Water (500 mL) was added and the phases were separated. The water phase was extracted with toluene and the combined organic phases were washed with water (2x) and brine. After drying over sodium sulfate, filtration and evaporation the crude mixture was treated with n-heptane (250 mL) and left in the freezer overnight. The solid was filtered off and the solvents of the filtrate were evaporated. This material was again taken up in n-heptane (100 mL) and kept in the freezer for three days. Filtration and evaporation of the solvent gave 2-(3,5-dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfide (41.6 g, 96% purity, 99% yield; E/Z=94/6—determined by GC).

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