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

Participants

Reaction Steps

A suspension of 2-bromo-4-fluoro-6-nitroaniline (14 g, 59 mmol) and SnCl2 (66 g, 295 mmol) in EtOH (50 mL) was heated at reflux for 5 h. The reaction mixture was concentrated in vacuo. To the residue was added EtOAc (100 mL) and satd. aq. NaHCO3 (200 mL). The mixture was filtered over Celite® and washed with EtOAc (100 mL×3). The combined organic layers were washed with satd. aq. NaHCO3, water, and brine, dried (MgSO4), filtered, and concentrated in vacuo to afford 3-bromo-5-fluorobenzene-1,2-diamine as a gray solid (10.1 g, 100%). MS (ESI): m/z=205 [M+1]+.

Provenance & Evidence