Nitric Acid → 5-Bromo-2-nitrobenzaldehyde

Participants

Reaction Steps

3-Bromo-benzaldehyde (18.50 g, 99.99 mmol) was added to a stirred solution of concentrated nitric acid (70%, 13.09 mL, 199.98 mmol) in concentrated sulfuric acid (125 mL) at 0° C. After the addition was complete, the ice bath was removed and the reaction was allowed to stir for 5 hours at room temperature. Then, the mixture was poured into ice and the solid was collected by filtration. The filtrate was extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was combined with the solid previously obtained via the first filtration and dissolved in diethyl ether. Hexanes were added and after crystallization 14.66 g (64%) of 5-bromo-2-nitro-benzaldehyde was collected by filtration and drying. 1H NMR (400 MHz, d6-DMSO): δ 10.19 (s, 1H), 8.10 (s, 2H), 8.02 (s, 1H).

Provenance & Evidence