Methanol → (2-Bromo-6-nitrophenyl)methanamine

Participants

Reaction Steps

A mixture of 1-bromo-2-fluoro-3-nitrobenzene (3.96 g, 18 mmol), 2M methylamine in MeOH (18 mL, 36 mmol) and DIPEA (3.3 mL, 19 mmol) was stirred for 3 h at RT. The reaction mixture was concentrated in vacuo. The resulting residue was taken up in DCM (100 mL) and washed with sat. NaHCO3 (100 mL). The aqueous layer was further extracted with DCM (100 mL). The combined organic fractions were washed with brine (50 mL), dried over Na2SO4 and concentrated in vacuo to afford the title compound as bright orange oil (4.16 g, 99%). LCMS (Method C): RT 3.39 min [M+H]+ 231 (for 79Br). 1H NMR (CDCl3, 400 MHz): δ 7.86 (1H, dd, J=8.5, 1.5 Hz), 7.67 (1H, dd, J=8.0, 1.5 Hz), 6.67 (1H, dd, J=8.5, 8.0 Hz), 3.13 (1H, bs), 3.01 (3H, d, J=5.5 Hz).

Provenance & Evidence