Benzene, 1-bromo-3-nitro- → 2-Bromo-6-nitroaniline

Participants

Reaction Steps

A mixture of 3-bromonitrobenzene (6.06 g, 30 mmol) and o-methylhydroxylamine hydrochloride (3.13 g, 37.5 mmol) were reacted in the presence of copper (I) chloride (0.59 g, 6 mmol) and potassium t-butoxide (10.1 g, 90 mmol) in DMF (75 mL). Aqueous work-up and chromatography gave 2-amino-3-bromonitrobenzene (0.36 g, 6%) as an orange powder. 1H NMR (CDCl3) δ 6.60 (t, 1H, J=9 Hz), 7.70 (d, 1H, J=9 Hz), 8.14 (d, 1H, J=9 Hz).

Provenance & Evidence