Tin dichloride dihydrate → 3-Bromo-N2-phenylbenzene-1,2-diamine

Participants

Reaction Steps

(2-Bromo-6-nitrophenyl)phenylamine (6.5 g, 22.7 mmol) was dissolved in EtOAc (100 mL) and SnCl2.H2O (25 g) added under a nitrogen atmosphere. The resulting mixture was heated at reflux for 5 h. The cooled reaction mixture was diluted with NaHCO3 (aq. satd. solution, 100 mL) and additional NaHCO3 added until all effervescence had ceased. The mixture was filtered through Celite® to remove insoluble inorganic material. The EtOAc layer was separated, washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by chromatography (Si—PCC, 0-50% EtOAc in cyclohexane) to give the product as a yellow crystalline solid (4.41 g, 77%). 1H NMR (300 MHz, CDCl3): δ 7.24-7.17 (2H, m), 7.01 (1H, dd, J=8.0, 1.5 Hz), 6.94 (1H, d, J=7.9 Hz), 6.85 (1H, dt, J=7.4, 1.0 Hz), 6.72 (1H, dd, J=7.9, 1.5 Hz), 6.67-6.61 (2H, m), 5.36 (1H, br s), 3.97 (2H, br s)

Provenance & Evidence