Stannous Chloride → 5-Bromo-2-fluoroaniline

Participants

Reaction Steps

Dissolve 4-bromo-1-fluoro-2-nitrobenzene (5.00 g, 22.73 mmol) and SnCl2 (dihydrate, 25.46 g, 113.6 mmol) in ethanol (100 mL) and heat to reflux overnight. Cool to room temperature and concentrate in-vacuo. Dissolve residue in ethyl acetate and basify with saturated aqueous NaHCO3. Filter through a pad of Celite and extract filtrate with ethyl acetate. Dry (MgSO4) and concentrate organics to a brown oil. Chromatograph on 90 g silica gel, eluting with 5% to 10% ethyl acetate/hexanes affords 2.85 g (66%) of the title compound as a tan oil. MS (ES) 191 (M+H); HPLC shows 99% purity.

Provenance & Evidence