Sodium Carbonate → 4-Bromo-3-chlorobenzene-1,2-diamine

Participants

Reaction Steps

To a stirred solution of 4-bromo-3-chloro-2-nitroaniline (0.200 g, 0.797 mmol) in EtOH (100 mL), was added SnCl2-2H2O (0.9 g, 3.985 mmol). The reaction mixture was heated to reflux for 3.5 h. The cooled solution (to rt) was diluted with H2O and the pH was adjusted to ca. 10 with Na2CO3. Extraction with CHCl3 (×3), was followed by washing with brine, drying over Na2SO4, and filtration. Concentration afforded an orange solid that was dried under vacuum to obtain 0.17 g product: 1H NMR (400 MHz, CDCl3) δ 6.92 (d, J=8.4 Hz, 1H), 6.51 (d, J=8.4 Hz, 1H), 3.90 (s, 2H), 3.40 (s, 2H); MS (ESI) m/z 223 (M+1).

Provenance & Evidence