Nitric Acid → HCID 67044866, compound

Participants

Reaction Conditions

Reaction Steps

2-[(4-chlorophenyl)carbonyl]-3,6-difluorobenzoic acid (3.20 g, 11.00 mmol) was dissolved while heating in concentrated.sulfuric acid (15 ml) and it was cooled to 0° C. A solution of fuming nitric acid (0.5 ml, 11.00 mmol) in concentrated.sulfuric acid (3.0 mL) was added dropwise and the reaction mixture was stirred at 0° C. for 60 minutes. It was poured into crushed ice. The product was precipitated. It was collected by filtration then it was dissolved in ethyl acetate (100 mL); it was washed with water (2×40 mL), brine (40 mL) and dried over anhydrous sodium sulfate. Filtration and concentration resulted in a crude product, which was triturated with hexane. The crystalline product was collected by filtration to give 2-[(4-chloro-3-nitrophenyl)carbonyl]-3,6-difluorobenzoic acid (2.73 g, 74% yield). 1H NMR (400 MHz, CD3OD): 8.28 (s, 1H), 7.91 (d, J=8.8 Hz, 1H), 7.79 (d, J=8.4 Hz, 1H), 7.53-7.42 (m, 2H); MS (EI) for C14H7ClF2NO5: 341 (M−).

Provenance & Evidence