Nitric Acid → HCID 53918291, compound

Participants

Reaction Conditions

Reaction Steps

2-Fluoro-5-hydroxy-4-propylbenzoic acid (500 mg, 2.52 mmol) was dissolved in nitromethane (50 mL) through heating to 40° C. and nitric acid (90%, 120 μL, 2.52 mmol) was added. After 10 min at 40° C. followed by reaction at room temperature for 2 h the solvent was evaporated. The residue was dissolved in EtOAc (150 mL), washed with brine (10 mL), dried (MgSO4) and concentrated to dryness giving 640 mg of crude product. Subsequent purification by flash chromatography (SiO2, EtOAc-HOAc 50:1) afforded pure 6-fluoro-3-hydroxy-2-nitro-4-propylbenzoic acid (294 mg). Mp: 128.0°-129.0° C. 1H NMR (DMSO-d6); δ10.2 (br, 1H), 7.39 (d, J=10.4 Hz, 1H), 2.63 (t, J=7.6 Hz, 2H), 1.55 (m, J=7.5 HZ, 2H), 0.89 (t, J=7.4 Hz, 3H). 13C NMR (DMSO-d6): δ162.49, 151.66 (d, J=245 Hz), 143.69, 138.74 (d, J=5 Hz), 138.17 (d, J=8 Hz), 120.25 (d, J=23 Hz), 113.82 (d, J=21 Hz), 31.44, 21.92, 13.60. MS (EI, 70 eV): m/z (rel. int) 243 (M+, 88).

Provenance & Evidence