Dimethylformamide → Methyl 2-phenylsulphenyl-4-trifluoromethylbenzoate

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Reaction Steps

A solution of 2-(phenylsulphenyl)-4-trifluoromethylbenzoic acid (11.5 g) and thionyl chloride (11.4 g) in dichloroethane containing a few drops of DMF was heated at reflux for 1.5 hours. The mixture was evaporated to dryness and methanol was added. The mixture was heated at reflux for 1 hour and evaporated to dryness. It was treated with water and extracted with ether, washed with sodium carbonate solution (2M), water, dried (Na2SO4) and filtered. The flitrate was evaporated to dryness and the residue was triturated with cyclohexane and filtered to give methyl 2-(phenylsulphenyl)-4-trifluoromethylbenzoate (10.5g) as a white solid, m.p. 55°-60° C.

Provenance & Evidence