2-BROMO-4-METHOXY-PHENYLAMINE

104-94-9

32338-02-6

General procedure for the synthesis of 2-bromo-4-methoxyaniline from 4-methoxyaniline: N-bromosuccinimide (NBS, 152 g, 853 mmol) was added batchwise to a tetrahydrofuran (THF, 3 L) solution of 4-methoxyaniline (100 g, 812 mmol) at -10 °C, keeping the temperature constant and stirring continuously for 30 min. After completion of the reaction, the mixture was concentrated under reduced pressure. The residue was purified by column chromatography (eluent: petroleum ether/ethyl acetate, 15:1, v/v) to afford the target product 2-bromo-4-methoxyaniline as a red oil (30.58 g, 18.6% yield). The nuclear magnetic resonance hydrogen spectrum (1H NMR, 400 MHz, CDCl3) data were as follows: δ = 7.01 (d, J = 2.4 Hz, 1H), 6.74-6.70 (m, 2H), 3.85-3.74 (m, 2H), 3.73 (s, 3H).