Nitric Acid → 5-Fluoro-2-methyl-3-nitrobenzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of 5-fluoro-2-methylbenzoic acid (from Matrix Scientific) in H2SO4 conc. (0.83 M) was cooled down to −10° C. Then, a mixture of fuming HNO3 conc. (2 eq.) and H2SO4 conc. (4 eq.) was added dropwise. After complete addition, the mixture was stirred at 0° C. for 1 h. The reaction mixture was poured onto ice/water and stirred for 10 min and then extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4) and solvent was removed in vacuo yielding the title compound as a yellow solid that was used without further purification in the next step. 1H NMR (300 MHz, DMSO-d6, 300 K) δ 13.86 (1H, bs), 8.09 (1H, dd, J=8.0 and 2.6 Hz), 7.90 (1H, dd, J=8.7 and 2.4 Hz), 2.50 (3H, s).

Provenance & Evidence