90-04-0

5473-01-8

Step A: Synthesis of 6-bromo-2-anisidine. A solution of bromine (1.22 mL, 23.7 mmol) in acetic acid (10 mL) was slowly added dropwise to a cooled solution of o-methoxyaniline (2.7 mL, 23.7 mmol) in hexadecanecarboxylic acid (20 mL) for a controlled time period of 10 minutes at 10°C. The reaction mixture was then stirred for 10 minutes. After the dropwise addition was completed, the reaction mixture was continued to be stirred for 10 min. Upon completion of the reaction, the solvent was removed by rotary evaporation and the residue was dissolved in ethyl acetate. The solution was sequentially washed with saturated sodium bicarbonate solution and dried with anhydrous magnesium sulfate. After drying, the desiccant was removed by filtration and the filtrate was concentrated by rotary evaporation. The crude product was purified by fast column chromatography on silica gel, the eluent being a hexane solution of 45% dichloromethane, resulting in 3.44 g of 2-bromo-6-methoxyaniline in 72% yield.