4-Bromo-2-(trifluoromethyl)aniline → HCID 86676831, compound

Participants

Reaction Conditions

Reaction Steps

To 4-bromo-2-(trifluoromethyl)aniline (4.61 g, 19.21 mmol) in H2O (24 mL), conc. HCl (4 mL) was added and stirred at 0° C. for 10 min. NaNO2 (1.32 g, 19.21 mmol), dissolved in water (10 mL), was added to the reaction mixture and allowed to stir at 0° C. for 30 min. The solid obtained was filtered, the filtrate was cooled to 0° C. and 2-oxocyclohexanecarboxylic acid (2.46 g, 19.21 mmol) was added while maintaining the temperature at 0° C. The reaction mixture was slowly warmed to room temperature and stirred for an additional 1 h. The solid obtained was filtered and air dried to afford the title compound (2 g, 30%). 1H NMR (200 MHz, CDCl3, δ in ppm) 14.05 (br s, 1H), 7.80-7.75 (d, J=8.8 Hz, 1H), 7.64-7.54 (m, 2H), 2.76-2.69 (m, 2H), 2.60-2.53 (m, 2H), 1.91-1.84 (m, 4H).

Provenance & Evidence