4-Fluoro-2-(trifluoromethyl)aniline → HCID 178471926, compound

Participants

Reaction Steps

A mixture of 4-fluoro-2-trifluoromethyl-aniline (5.0 g, 27.89 mmol) and 2-benzoyl-3-ethoxy-acrylic acid ethyl ester (6.9 g, 27.89 mmol) in toluene (125 mL) was heated at reflux. After 18 hr, the reaction was cooled, concentrated and purified by column chromatography (eluent 10% to 40% Et2O/hexanes) to give 2-benzoyl-3-(2-trifluoromethyl-4-fluoro-phenylamino)-acrylic acid ethyl ester (6.6 g, 62%); MS (ESI) m/z 382 (M+H)+; 1H NMR E:Z (mixture 1:1) (CDCl3): δ 0.88 (t, J=5.38 Hz, 3H), 0.95 (t, J=5.38 Hz, 3H), 4.02 (q, J=5.38 Hz, 2H), 4.07 (t, J=5.38 Hz, 2H), 7.29-7.51 (m, 10H), 7.53-7.56 (dt, J=9.67, 1.54 Hz, 2H), 7.66-7.68 (dt, J=8.33, 1.41 Hz, 2H), 8.10-8.13 (d, J=12.68 Hz, 2H), 8.36-8.39 (d, J=12.43 Hz, 2H), 11.17-11.20 (d, J=12.68 Hz, 1H), 12.39-12.42 (d, J=12.43 Hz, 1H).

Provenance & Evidence