2-Benzyloxy-5-nitroiodobenzene → 4-(Benzyloxy)-3-iodobenzenamine

Participants

Reaction Conditions

Reaction Steps

Iron powder (12.5 g, 224 mmol) was added to a suspension of 2-benzyloxy-5-nitroiodobenzene (Description 13; 10 g, 28 mmol) in water (300 ml) and acetic acid (75 ml) and the mixture was stirred at 80° C. for 12 hours. The mixture was allowed to cool to room temperature and filtered through Hyflo™, washing with 4:1 water:acetic acid and ethyl acetate. The filtrate was extracted with ethyl acetate, and the organic extract was evaporated under reduced pressure. Saturated aqueous sodium hydrogen carbonate was added and the mixture was extracted with ethyl acetate. The organic extract was washed with brine, dried (MgSO4), and the solvent was evaporated under reduced pressure to give the title compound as a brown oil (9 g, 99% yield). 1H NMR (360 MHz, CDCl3) δ 7.49−7.47 (2H, m), 7.40−7.28 (3H, m), 7.19 (1H, d, J 2.4 Hz), 6.70 (1H, d, J 8.6 Hz), 6.62 (1H, dd, J 2.4, 8.6 Hz), and 5.04 (2H, s). m/z (ES+) 326 (M+1)+.

Provenance & Evidence