2-Bromo-5-nitroanisole

97-52-9

77337-82-7

General procedure for the synthesis of 2-bromo-5-nitroanisole from 2-methoxy-4-nitroaniline: a catalytic amount of copper bromide (1 mol%) was added to a solution of 2-methoxy-4-nitroaniline (2.5 mmol) in acetonitrile (30 ml), followed by camphorsulfonic acid (3.0 mmol), sodium nitrite or tert-butyl nitrite (3.0 mmol), and tetrabutylammonium bromide (5.0 mmol). The reaction mixture was stirred at 60°C for 24 h (Tables 1 and 2). Nitrogen release was observed immediately during the reaction. After completion of the reaction (confirmed by β-naphthol test and thin layer chromatography), the solvent was removed using a rotary evaporator. The residue was washed with water and extracted with dichloromethane. The organic phases were combined, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. Finally, purification by column chromatography using a hexane/dichloromethane solvent mixture as eluent gave the pure product 2-bromo-5-nitroanisole. The physical properties and 1H NMR data of the product were consistent with the commercially available analytically pure sample.