Synthesis
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).
References
[1] Russian Journal of Applied Chemistry, 2009, vol. 82, # 9, p. 1570 - 1576
[2] Journal of the Chilean Chemical Society, 2011, vol. 56, # 4, p. 863 - 865
[3] Organic Letters, 2006, vol. 8, # 19, p. 4291 - 4293
[4] Journal of the Brazilian Chemical Society, 2010, vol. 21, # 3, p. 496 - 501
[5] Synthetic Communications, 2010, vol. 40, # 6, p. 868 - 876
