Water → 4-Bromo-3-methyl-2-nitroaniline

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Reaction Steps

3-methyl-2-nitroaniline (6.2 g, 41 mmol) was dissolved in 150 mL acetic acid, stirred and treated in portions with N-bromosuccinimide (7.3 g, 41 mmol). After 1 h the mixture was poured into 400 mL water with stirring. The precipitated product was collected by filtration, washed well with water, and then taken up in 200 mL ethyl acetate. This solution was washed with 50 mL water, 50 mL saturated NaHCO3, 50 mL saturated NaCl, dried (Na2SO4) and evaporated under vacuum to give the title compound as a bright orange solid (8.2 g, 87%): 1H NMR (400 MHz, CDCl3) δ 7.44-7.33 (d, J=8.8 Hz, 1H), 6.62-6.49 (d, J=8.8 Hz, 1H), 4.75 (s, 2H), 2.41 (s, 3H); EIMS m/z 230.

Provenance & Evidence