[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15].ClC1C=CC=C(C(OO)=[O:26])C=1>ClCCl.CO>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[N+:11]([O-:26])[CH:12]=[C:13]([CH:17]=1)[C:14]([OH:16])=[O:15]To a solution of 5-(2-fluoro-4-methylphenyl)nicotinic acid (0.15 g, 0.43 mmol) in dichloromethane (5 mL) and methanol (3 mL) was added 3-chloroperbenzoic acid (70%; 0.16 g, 0.65 mmol). The mixture was stirred at ambient temperature. After 18 h, additional 3-chloroperbenzoic acid (70%; 0.19 g, 0.86 mmol) was added. The mixture was continued to stir at ambient temperature. After 24 h, additional 3-chloroperbenzoic acid (70%; 0.19 g, 0.86 mmol) was added. After 18 h, the mixture was concentrated. Purification by reverse chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (70 mg). MS 248.0 (M+1).
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