Ammonium Chloride → 5-Bromo-3-fluorobenzene-1,2-diamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-2-fluoro-6-nitroaniline (0.5 g, 2.1 mmol) in THF (4.6 mL), EtOH (4.6 mL) and H2O (1.5 mL) was added iron powder (0.6 g, 10.6 mmol) and ammonium chloride (0.17 g, 3.2 mmol). The resulting mixture was stirred at 95° C. for 22 hours. The mixture was cooled to room temperature and filtered through diatomaceous earth. The solid was washed with EtOH until no further color came through the filter. The filtrate was concentrated and the residue was dissolved in EtOAc, washed with H2O and brine, dried over Na2SO4, filtered and concentrated to give the title compound (0.43 g, 99%) as a brown, waxy solid.

Provenance & Evidence