Ethanolamine → 2-[(2-Bromo-6-nitrophenyl)amino]ethanol

Participants

Reaction Steps

A solution of 1-bromo-2-chloro-3-nitrobenzene (0.34 g, 1.4 mmol) and ethanolamine (0.22 mL, 3.5 mmol) in dry ethanol (3.8 mL) was irradiated in a microwave oven at 135° C. for 180 min. After the reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, the organic phase was washed with potassium bisulfate (0.1 M), water and brine, dried over Na2SO4 and concentrated. Purification was performed using flash chromatography on a silica column and 25% ethyl acetate in heptane as an eluent to yield 2-[(2-bromo-6-nitrophenyl)amino]ethanol as red oil, 0.24 g (65%). 1H NMR (400 MHz, DMSO-D6) δ ppm 3.13 (q, J=5.2 Hz, 2H) 3.51 (q, J=5.1 Hz, 2H) 4.87 (t, J=5.1 Hz, 1H) 6.18 (t, J=5.1 Hz, 1H) 6.80 (t, J=8.1 Hz, 1H) 7.84 (dd, J=7.8, 3.3 Hz, 2H).

Provenance & Evidence