Chlorosuccinimide → 2-Chloro-4-(trifluoromethoxy)aniline

Participants

Reaction Steps

Part A. A solution of 4-trifluoromethoxyaniline (12.0 mL, 88.8 mmol) and N-chlorosuccinimide (13.04 g, 97.7 mmol) in acetonitrile (90 mL) was heated to reflux for 12 h. After cooling, the solution was filtered and evaporated, and the residual material was separated by column chromatography (silica gel, 10:90 ethyl acetate-hexane) to afford the product, 2-chloro-4-trifluoromethoxyaniline, as a liquid. The product was further purified by distillation to afford 18.14 g (85.7 mmol, 97%) pure product, b.p. 50-60° C./5 mm Hg (bulb-to-bulb). 1H NMR (300 MHz, CDCl3): Δ 7.16 (1H, d, J=2.5 Hz), 6.96 (1H, dd, J=8.8, 2.5 Hz), 6.73 (1H, d, J=8.8 Hz), 4.08 (2H, br s). MS (H2O-GC/MS): m/e 214 (27), 213 (17), 212 (100).

Provenance & Evidence