General procedure for the synthesis of 2-bromo-6-nitroanisole from 2-bromo-6-nitrophenol (19.6 g, 90.0 mmol) and iodomethane (25.6 g, 180 mmol): first, 2-bromo-6-nitrophenol and potassium carbonate (24.9 g, 180 mmol) were mixed in acetone (400 mL). Subsequently, iodomethane was added to the mixture. The reaction mixture was heated to reflux overnight. After completion of the reaction, it was cooled to room temperature, the mixture was filtered and the filter cake was washed with ethyl acetate (100 mL). The filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the resulting solution was washed with saturated brine and dried with anhydrous sodium sulfate. Finally, the dried solution was concentrated to give 1-bromo-2-methoxy-3-nitrobenzene (20.2 g, 97% yield) as a yellow solid. The 1H-NMR spectrum (300 MHz, DMSO-d6) data of the product were as follows: δ (ppm): 3.92 (s, 3H), 7.32 (d, 1H, J = 8.1 Hz), 7.94-8.03 (m, 2H).
