Stannous Chloride → 3-Bromobenzene-1,2-diamine

Participants

Reaction Steps

A suspension of 2-bromo-6-nitrobenzenamine (2.0 g, 9 mmol) and SnCl2 (10.2 g, 54 mmol) in EtOH (20 mL) was heated at reflux for 2 h, then cooled to RT and concentrated in vacuo. The residue was diluted with EtOAc (100 mL) and washed with saturated NaHCO3 solution (200 mL). The resulting slurry was filtered through a pad of Celite® and washed with EtOAc (50 ml, ×3). The filtrate was washed with saturated NaHCO3, water, and brine, dried (MgSO4), filtered and concentrated in vacuo to afford 3-bromobenzene-1,2-diamine as a brown oil (1.5 g, 90%). MS (ESI): m/z=186.9 [M+1]+.

Provenance & Evidence