Ammonium Chloride → 5-Bromo-4-fluoro-2-methylaniline

Participants

Reaction Conditions

Reaction Steps

A mixture of iron powder (4.30 g) and ammonium chloride (1.143 g) in water (23 mL) was heated under reflux at 100° C. for 30 minutes. To this hot mixture was added 1-bromo-2-fluoro-4-methyl-5-nitrobenzene (5.00 g) slowly and then the reaction mixture was heated under reflux at 100° C. overnight. The mixture was cooled to room temperature, filtered through a pad of celite, and extracted with ethyl acetate (3×50 mL). The organic solution was washed with water (3×100 mL) and brine (100 mL), dried (MgSO4) and concentrated under reduced pressure to give the subtitle compound (3.59 g) as a solid. 1H NMR δ (CDCl3) 6.86-6.79 (m, 2H), 3.49 (s, 2H), 2.11 (s, 3H)

Provenance & Evidence