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

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To a suspension of 1-bromo-2,4-difluorobenzene (11.7 mL, 104 mmol) in 96 mL concentrated H2SO4 at 0° C. was added concentrated HNO3 (85 mL) dropwise maintaining the temperature below 20° C. The resulting mixture was stirred for 10 minutes at 0° C., then poured into a mixture of ether and ice water with vigorous stirring. The aqueous phase was separated and extracted with ether. The combined organic phases were washed with aqueous NaHCO3 and brine, dried and concentrated. The residue was purified using silica gel column chromatography with 15% acetone in hexanes to provide 1-bromo-2,4-difluoro-5-nitrobenzene (23 g, 96.6 mmol, 93.3% yield) as yellow oil.

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