Potassium peroxymonosulphate → 4-[(4-Fluorophenyl)ethynyl]benzoic acid

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[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.S([O-])(O[O-])(=O)=[O:19].[K+].[K+]>CN(C=O)C.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[C:9][C:10]2[CH:11]=[CH:12][C:13]([C:14]([OH:19])=[O:15])=[CH:16][CH:17]=2)=[CH:6][CH:7]=1

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실험 절차

To a solution of 4-[(4-fluorophenyl)ethynyl]benzaldehyde (10.39 g; 46.37 mmol, intermediate which may be obtained according to methods disclosed in EP03 103780.7) in DMF (400 mL) was added potassium peroxomonosulfate (28.5 g, 46.4 mmol) in one portion at rt. The reaction mixture was stirred at rt overnight. The reaction mixture was poured in water (2 L) and the resulting precipitate was filtered off, washed with water and dried under reduced pressure to give 10.45 g (94%) of the title compound as a white powder. HPLC, Rt: 3.98 min (purity: 98.6%). 1H NMR (DMSO-d6) δ: 13.15 (brs, 1H), 7.96 (d, J=8.1 Hz, 2H), 7.64 (m, 4H), 7.29 (t, J=8.9 Hz, 2H).