95668-21-6

2267-23-4

95668-21-6

General procedure for the synthesis of 3-nitro-4-bromotrifluoromethoxybenzene from 2-nitro-4-trifluoromethoxyaniline: tert-butyl nitrite (7.4 g, 72 mmol) was added to a solution of 2-nitro-4-[(trifluoromethyl)oxy]aniline (2.0 g, 9.0 mmol) in acetonitrile (50 mL). The reaction mixture was stirred for 2 minutes and then copper(II) bromide (40 g, 180 mmol) was added. Stirring of the reaction mixture was continued for 1 hour at room temperature. Upon completion of the reaction, the reaction mixture was partitioned between ethyl acetate (500 mL) and aqueous 1N hydrochloric acid (100 mL). The organic layer was separated and washed with 1N aqueous hydrochloric acid solution (3 x 50 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by fast column chromatography (eluent: 0 to 20% ethyl acetate/hexane) to afford 3-nitro-4-bromotrifluoromethoxybenzene 2.0 g (78% yield).1H NMR (400 MHz, CDCl3): δ 7.78 (d, J = 8.79 Hz, 1H), 7.76 (s, 1H), 7.32 (d, J = 8.79 Hz, 1H ).