5-BROMO-2-METHOXYANILINE

33696-00-3

6358-77-6

General procedure for the synthesis of 5-bromo-2-methoxyaniline from 2-nitro-4-bromoanisole: 1. Preparation of Intermediate 11A: An ethanol (65 mL) solution of 4-bromo-1-methoxy-2-nitrobenzene (2.00 g, 8.62 mmol), zinc powder (5.64 g, 86.0 mmol), and ammonium chloride (4.61 g, 86.0 mmol) was stirred for 2 hours at room temperature. 2. Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate (EtOAc) and filtered through diatomaceous earth (CELITE). 3. The filtrate was concentrated by evaporation to give Intermediate 11A (1.74 g, 100% yield) as an off-white solid. 4. Mass spectral analysis (LCMS-ESI) of Intermediate 11A showed m/z 202,204 ([M+H]? , [M+2+H]?) , and a retention time (RT) of 0.70 min (Method J).