Thionyl Chloride → 2-Vinylphenyl 4-(trifluoromethyl)benzenesulfonate

Participants

Reaction Steps

A dry, air-free, ice-cold solution of 2-formylphenyl 4-(trifluoromethyl)-benzenesulfonate (2.0 g, 6.1 mmol) in THF (7 mL) is treated with 6.8 mL of 1 M (trimethylsilylmethyl)magnesium chloride in diethyl ether. The reaction is stirred 30 minutes. Thionyl chloride (0.5 mL, 6.9 mmol) is added and the reaction is stirred at 0° C. for 1 h. The reaction is quenched with ice and extracted with ethyl acetate. The product is purified on silica gel in methylene chloride. A yield of 1.8 g of 2-vinylphenyl 4-(trifluoromethyl)benzenesulfonate is obtained.

Provenance & Evidence