Bromine → 2-Bromo-4-fluoro-6-nitroaniline

Participants

Reaction Steps

A solution of 4-fluoro-2-nitroaniline (39.03 g, 250 mmol) in water (900 ml) and 48% hydrobromic acid (1500 ml) was treated with bromine (15.26 ml, 46 g, 288 mmol) added dropwise over 20 min. The resulting precipitate was stirred at ambient temperature for a further 45 min then diluted with ice-water (2000 ml). The solid product was collected by filtration, washed with cold water and dried to afford 2-bromo-4-fluoro-6-nitrophenylamine as an orange powder (55 g, 94%): δH (360 MHz, CDCl3) 6.49 (2H, br), 7.56 (1H, dd, J 7 and 3), 7.90 (1H, dd, J 9 and 3).

Provenance & Evidence