Stannous Chloride → 4-Bromo-5-fluoro-1,2-benzenediamine

Participants

Reaction Steps

To a suspension of 96 (1.57 g, 6.74 mmol) in EtOH (16 mL) was added SnCl2 (3.82 g, 20.2 mmol). The reaction mixture was heated at reflux for 14 h, cooled to RT and concentrated in vacuo. The residue was partitioned between EtOAc (100 mL) and sat'd. aq. NaHCO3 (200 mL). The resulting slurry was filtered through a pad of Celite® and the wet cake was washed with EtOAc (3×50 mL). The organic layer was washed sequentially with saturated NaHCO3, water, and brine, dried (MgSO4), filtered and concentrated in vacuo to afford 600 mg (43%) of 4-bromo-5-fluorobenzene-1,2-diamine (98) as yellow solid: MS (ESI) m/z=205 [M+1]+.

Provenance & Evidence