Potassium Nitrate → 2-Fluoro-5-methoxycarbonyloxy-4-methylnitrobenzene

Participants

Reaction Conditions

Reaction Steps

To a solution of carbonic acid 4-fluoro-2-methyl-phenyl ester methyl ester (15 g, 81.5 mmol) in conc. sulfuric acid (100 mL) at 0° C. was added powdered KNO3 (8.3 g, 82.2 mmol) in several portions. The reaction mixture was stirred for 1 hour at 0° C. and was then poured into ice water and extracted with ethyl acetate (3×100 mL). The extracts were washed with water and brine, dried (MgSO4), concentrated in vacuo and purified by silica gel chromatography to provide carbonic acid 4-fluoro-2-methyl-5-nitro-phenyl ester methyl ester (2.0 g, 11% yield). 1H NMR (300 MHz, DMSO-d6): δ 8.14 (d, J=6.9, 1 H), 7.60 (d, J=12.0 Hz, 1H), 3.86 (s, 3H), 2.25 (s, 3H).

Provenance & Evidence