2-Bromo-1-nitro-4-(trifluoromethyl)benzene

57946-63-1

132839-58-8

The general procedure for the synthesis of 2-bromo-4-trifluoromethylnitrobenzene (95% content) from 2-bromo-4-(trifluoromethyl)aniline was as follows: the compound was prepared by oxidizing 4-(trifluoromethyl)aniline. To a 300 mL three-necked round-bottomed flask equipped with a reflux condenser and a dropping funnel was added sodium perborate tetrahydrate (40.69 g, 0.264 mol) and glacial acetic acid (50 mL). 2-Bromo-4-(trifluoromethyl)aniline (6.31 g, 26.8 mmol) and glacial acetic acid (50 mL) were added to the dropping funnel. The suspension in the flask was heated to 55°C and the contents of the dropping funnel were slowly added dropwise.After 3 h, additional sodium perborate tetrahydrate (20.00 g, 0.130 mol) was added to the reaction mixture and stirring was continued at 55°C for 4 h. The reaction was carried out at 55°C. The yellow suspension obtained from the reaction was cooled to room temperature and filtered through a diatomaceous earth pad. The organic phase was separated by adding ether (200 mL) and water (100 mL) to the filtrate. The aqueous phase was extracted twice with diethyl ether (150 mL x 2). The combined organic phases were separated by neutralization with 3M aqueous sodium hydroxide solution. The separated organic phase was dried with sodium sulfate and then concentrated to give a brown liquid. The crude product was purified by fast column chromatography (12% EtOAc/hexane) to give 2-bromo-4-trifluoromethylnitrobenzene (95% content) as a final yellow liquid (4.22 g, 60% yield).