Sulfuric Acid → Methyl 2-bromo-4-fluoro-5-nitrophenoxyformate

Participants

Reaction Conditions

Reaction Steps

(2-Bromo-4-fluoro-phenyl) methyl carbonate (8.25 g, 33.13 mmol) was added portionwise to conc. H2SO4 (45 mL) to generate a colorless homogeneous solution. This solution was then cooled to 0° C. and KNO3 (3.7 g, 36.44 mmol) was added portionwise maintaining the internal temperature below 5° C. The reaction was stirred for 2 h and then poured on ice-water and the aqueous layer was extracted with DCM (3×10 mL). The combined organic layer was dried over Na2SO4, filtered and concentrated. The residue was then purified by silica gel column chromatography using 15% EtOAc/hexane gradient to yield 2-bromo-4-fluoro-5-nitrophenyl methyl carbonate (8.93 g, 92%) 1H NMR (400 MHz, CDCl3) δ 8.05 (d, J=6.7 Hz, 1H), 7.65 (d, J=9.6 Hz, 1H), 4.01 (s, 3H).

Provenance & Evidence