Synthesis of 5-bromo-2-(trifluoromethoxy)aniline (1): to a solution of 4-bromo-2-nitro-1-(trifluoromethoxy)benzene (2.0 g, 7.0 mmol) in acetic acid (10.0 mL) was added powdered iron (1.0 g, 17.9 mmol) batchwise at 0-10 °C. The reaction mixture was stirred at room temperature for 2 hours. Upon completion of the reaction, the acetic acid was removed by distillation and the residue was diluted with water and the pH was adjusted to alkaline with saturated sodium bicarbonate solution. Subsequently, the aqueous phase was extracted with ethyl acetate (2 x 50 mL). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the brown colloidal solid product 1 (1.2 g, 70% yield).1H NMR (400 MHz, DMSO-d6): δ 5.68 (s, 2H), 6.65-6.66 (dd, J=2.4 Hz, 6.2 Hz, 1H), 6.95-6.96 (d, J=2.5 Hz. 1H), 7.01-7.01 (dd, J=1.4Hz, 8.6Hz, 1H). ms m/z (M+H): 256.3.
