[N+:1]([O-:4])(O)=[O:2].[F:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([O:15][CH3:16])[CH:14]=1)[C:9]([OH:11])=[O:10].C([O-])(O)=O.[Na+]>C(O)(=O)C>[F:5][C:6]1[CH:14]=[C:13]([O:15][CH3:16])[C:12]([N+:1]([O-:4])=[O:2])=[C:8]([CH:7]=1)[C:9]([OH:11])=[O:10]To a solution of fuming nitric acid (18 mL) and glacial acetic acid (36 mL) preheated to 55° C. was added 3-fluoro-5-methoxybenzoic acid (3.00 g, 17.63 mmol) portion wise over 5 min. The mixture was maintained at 55° C. for an additional 90 min. The reaction was cooled to ambient temperature and poured onto ice-water (200 mL). The pH of the solution was adjusted to 2 using aqueous NaHCO3 solution. The precipitate formed was filtered and washed with hexanes (100 mL) to afford 5-fluoro-3-methoxy-2-nitrobenzoic acid (2.52 g, 66%) as a white solid. 1H NMR and MS consistent.
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