[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([CH3:18])=[CH:15][CH:16]=3)[O:11][C:10](=[O:19])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.[Br:20]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH2:18][C:14]1[CH:13]=[C:12]2[C:17]([C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)=[CH:9][C:10](=[O:19])[O:11]2)=[CH:16][CH:15]=1To a solution of 4-(3-fluorophenyl)-7-methyl-2H-chromen-2-one (1.25 g, 4.9 mmol) in carbontetrachloride (30 mL), N-bromosuccinimide (963 mg, 5.41 mmol) and benzoylperoxide (60 mg, 0.25 mmol) were added. The reaction was then stirred overnight at reflux. After cooling, the reaction mixture was concentrated under reduced pressure. The crude residue obtained was purified on a short column of silica gel (eluting with CH2Cl2). The filtrate was concentrated and the solid obtained was swished in a mixture of CH2Cl2/hexanes. The title product was collected by filtration. 1H NMR (400 MHz, acetone-d6): 7.72-7.6 (m, 1H), 7.55 (s, 1H), 7.47 (s, 1H), 7.45-7.3 (m, 4H), 6.4 (s, 1H), 4.78 (s, 2H).
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