Methylamine → 5-bromo-N-methyl-2-nitroaniline

Participants

Reaction Steps

A solution of 4-Bromo-2-fluoronitrobenzene (1-1, 10.5 g, 47.7 mmol) in EtOH (100 ml) was treated with Methylamine (2M in MeOH, 28.6 ml, 57.3 mmol, 1.2 eq) and the resulting dark maroon solution was stirred at 23 deg C. for 13 h. The reaction was then concentrated in vacuo, and the residual yellow-orange solid was partitioned between EtOAc (2×250 ml) and water (300 ml). The combined organic layers were dried over Na2SO4 and concentrated, leaving the title compound, 5-bromo-N-methyl-2-nitroaniline (1-2), as a bright orange solid. 1H NMR (300 MHz, CDCl3) δ 8.03 (d, 1H, J=9.15 Hz), 7.01 (sd, 1H, J=1.83 Hz), 6.77 (dd, 1H, J=7.02 Hz), 3.02 (d, 3H, J=4.88 Hz). LRMS m/z: Calc'd for C7H7BrN2O2 (M+H) 232.1, found 232.8.

Provenance & Evidence