Nitric Acid → 1-Bromo-2,4-difluoro-5-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

To a suspension of 1-bromo-2,4-difluorobenzene (53.0 mmol, 6.00 mL) in concentrated H2SO4 (38.5 mL) at 0° C. was added dropwise concentrated HNO3 (34.0 mL) maintaining internal temperature below 20° C. The resulting mixture was stirred for 10 min at 0° C., then poured into ice/water with vigorous stirring. The mixture was extracted with Et2O (3×100 mL). The combined organic extracts were washed with aqueous NaHCO3 solution (3×100 mL) and brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (EtOAc:hexanes 1:9) to afford 5-bromo-2,4-difluoronitrobenzene as a yellow oil (12.2 g, 97%). 1H NMR (400 MHz, CDCl3) δ 8.45 (t, 1H, J=7.5 Hz), 7.16 (dd, 1H, J=11.0, 8.6 Hz); ESMS m/e: 240, 238, 223, 221, 112

Provenance & Evidence