Water → 5-bromo-2-nitro-n-phenylaniline

Participants

Reaction Steps

To a solution of 4-bromo-2-fluoro-1-nitrobenzene (1.0 g, 4.58 mmol) and diisopropyl ethylamine (1.1 mL, 6.87 mmol) in NMP (10 mL) was added aniline (0.51 g, 5.49 mmol). The solution was stirred for 14 h to which was slowly added H2O (5 mL). The resulting yellow precipitate was filtered, washed with 5 mL of water, dried (high vacuum, 14 h) to furnish N-phenyl-5-bromo-2-nitrobenzenamine (1.2 g), 90% yield. 1H NMR (500 MHz, CDCl3): δ 6.92 (dd, J=2 Hz, 1H), 7.35 (m, 5H), 7.51 (m, 1H) 8.11 (d, J=9.0 Hz, 1H), 9.55 (bs, 1H).

Provenance & Evidence