2-(3-Bromo-propoxy)-5-nitro-biphenyl → 6-(3-Bromo-propoxy)-biphenyl-3-ylamine

Participants

Reaction Steps

2-(3-Bromo-propoxy)-5-nitro-biphenyl (q, 530 mg, 1.57 mmol) was refluxed with stannous chloride hydrate (1.1 g, 4.8 mmol) in 5 mL ethanol and 3 mL concentrated HCl. After 1.5 hours, the solvent was evaporated and the mixture was basified with 2N NaOH. The mixture was then extracted with DCM, dried and evaporated, affording 250 mg 6-(3-bromo-propoxy)-biphenyl-3-ylamine (r) in 50% yield: 1H NMR (500 MHz, CDCl3): 7.3 (m, 5H), 6.7 (m, 3H), 4.2 (bs, 2H), 3.9 (m, 2H), 3.5 (m, 2H) and 2.1 (2H).

Provenance & Evidence