[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[Br:14]N1C(=O)CCC1=O.N(C(CC)C#N)=NC(CC)C#N.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(OCC)(=O)C>[Br:14][CH2:13][C:12]1[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]=1[F:1]To a solution (11 ml) of the compound (2.0 g, 11 mmol) obtained in Example 189a in ethyl acetate were added N-bromosuccinimide (2.9 g, 17 mmol) and 2,2′-azobisbutyronitrile (AIBN) (180 mg, 1.1 mmol), and the mixture was heated under reflux for 5 hr under light irradiation. An aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-hexane/ethyl acetate=90/10) to give a crude title compound (2.3 g, 81%) as a colorless oil.
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