2-Methoxy-4-nitroaniline → 2-bromo-6-methoxy-4-nitroaniline

Participants

Reaction Steps

A clear yellow solution of 2-methoxy-4-nitroaniline (10 g, 15 59.5 mmol) in acetonitrile (300 mL) at room temperature was treated with N-bromosuccinimide (10.58 g, 59.5 mmol). The reaction was protected from light and stirred for 2 hours at room temperature. TLC (3:1 hexane:ethyl acetate) analysis showed starting material (Rf 0.14) replaced with a higher spot (Rf 0.23). The reaction was concentrated in vacuo, treated with carbon tetrachloride, filtered through celite and concentrated in vacuo to give 2-bromo-6-methoxy-4-nitroaniline as a yellow brown solid. 1H NMR (δ, CDCl3): 8.11 (1H, d, J=2.2 Hz), 7.63 (1H, d, J=2.2 Hz), 4.96 (2H, br s), 3.96 (3H, s); MS (m/z) 249, 247.

Provenance & Evidence