Ammonia → 4-(Trifluoromethylthio)toluene

Participants

Reaction Conditions

Reaction Steps

p-Toluenethiol (8 g.) was added to liquid ammonia (60 ml.) at -30°. Trifluoromethyl iodide (18 g.) was added and the mixture was irradiated with uv light (297nm.) for 30 minutes. Dry diethyl ether (35 ml.) was added and irradiation was continued for 1 hour. The mixture was allowed to warm to 20° C. and water was added. The mixture was extracted with diethyl ether and the ethereal extracts were washed with sodium thiosulphate solution and then water. The ethereal extracts were dried over anhydrous magnesium sulphate and evaporated in vacuo. Distillation gave 4-trifluoromethylthiotoluene as a mobile yellow-brown liquid (b.p. 78°-80° C., 16 mm.).

Provenance & Evidence