4-Bromo-2-(trifluoromethoxy)aniline

clear pale yellow to orange-yellow liquid

4-Bromo-2-(trifluoromethoxy)aniline is a versatile building block that can be used to create a range of compounds, such as methyl 4- amino-3-(trifluoromethoxy)benzoate, 1-Bromo-3-(trifluoromethoxy)benzene, etc.
To a solution of 4-bromo-2-(trifluoromethoxy)aniline (10 g, 50.21 mmol) in methanol (150 mL) in a pressure tank reactor was added TEA (11.84 g, 117.01 mmol), Pd(dppf)Ci2 CH2Q2 (2.4 g, 2.94 mmol). Then the reactor was charged with CO (g) (20 atm). The resulting reaction was stirred for 1.5 days at 100°C. Then it was diluted with water (200 mL), extracted with ethyl acetate (3 x 100 mL) and the organic layers combined and dried in an oven under reduced pressure. The resulting mixture was concentrated in a vacuo. The residue was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:50) to afford methyl 4- amino-3-(trifluoromethoxy)benzoate as yellow solid (5 g, 54 %).