Acetic Acid → 2-Bromo-7-nitronaphthalene

Participants

Reaction Steps

To a solution of NaNO2 (1.1 g, 24 mmol) in sulfuric acid (8.4 ml) was added at 0° C. acetic acid (8.9 ml) and 7-amino-2-nitro-naphthalene (2.1 g, 1mmol). This solution was added to a suspension of CuBr (2.5 g, 39 mmol) in conc. HBr (16 ml) at 0° C. and the mixture was stirred for 1 hour. The mixture was poured on ice and the aqueous phase was extracted with methylene chloride. The crude product was purified by chromatography to give 1.9 g (7.4 mmol, 51%) of the title compound, MS: m/e=251.2 (M+).

Provenance & Evidence