3-(Trifluoromethyl)aniline → 1-Isothiocyanato-3-(trifluoromethyl)benzene

Participants

Reaction Steps

To a stirred solution of 3-(trifluoromethyl)aniline (20 g, 124.2 mmol) in DCM (100 mL) was added thiophosgene (21.24 g, 186.4 mmol) at 5-10° C. and the reaction mixture was stirred at room temperature for 1-2 h. The reaction was monitored by TLC (mobile phase-40% ethyl acetate in n-Hexane, Rf. S.M.—0.25, product—0.5). Upon disappearance of the starting material, the reaction mass was diluted with DCM, the organic layer was washed with 10% NaHCO3, water and brine. The organic layer was dried and concentrated in vacuo at a temperature lower than 45° C. to afford the product as a yellow oil (Yield: 19.2 g, 76.19% of theoretical).

Provenance & Evidence