[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])=[CH:4][C:3]=1[CH3:16].[Br:17]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(OCC)(=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][Si:7]([C:10]([CH3:11])([CH3:12])[CH3:13])([CH3:8])[CH3:9])=[CH:4][C:3]=1[CH2:16][Br:17]To a solution of (4-bromo-3-methylphenoxy)(tert-butyl)dimethylsilane (6.97 g) and N-bromosuccinimide (6.21 g) in ethyl acetate (100 mL) was added 2,2′-azobis(isobutyronitrile) (383 mg), and the mixture was refluxed for 17 hr. The mixture was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.65 g) as a colorless oil.
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