Nitric Acid → 5-Bromo-4-fluoro-2-nitrobenzaldehyde

Participants

Reaction Steps

4-Fluoro-3-bromo-benzaldehyde (3.00 g, 14.78 mmol) was added to a stirred solution of concentrated nitric acid (67%, 2.02 mL, 29.55 mmol) in concentrated sulfuric acid (18 mL) at 0° C. After the addition was complete, the ice bath was removed and the reaction was allowed to stir for 3 hours at room temperature. Then, the mixture was poured into ice and extracted with diethyl ether. The organic layer was dried over anhydrous magnesium sulfate, then filtered and concentrated. The residue was purified by silica gel chromatography eluting with 1:9 ethyl acetate:hexanes to give 2.66 g (73%) of 5-bromo-4-fluoro-2-nitro-benzaldehyde as a solid. 1H NMR (400 MHz, d6-DMSO): δ 10.14 (s, 1H), 8.31 (d, J=8 Hz, 1H), 8.25 (d, J=7 Hz, 1H).

Provenance & Evidence