[CH3:1][Si:2]([O:5][C:6](=[O:10])/[CH:7]=[CH:8]/[CH3:9])([CH3:4])[CH3:3].[Br:11]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:1][Si:2]([O:5][C:6](=[O:10])/[CH:7]=[CH:8]/[CH2:9][Br:11])([CH3:4])[CH3:3]A stirred mixture of trimethylsilylcrotonate (131 g, 0.828 mol), N-bromosuccinimide (206 g, 1.16 mol), benzoyl peroxide (3.41 g, 0.141 mol) and carbon tetrachloride (1 L) is warmed to reflux (77° C.) under visible light for 5 hours. The mixture is cooled to room temperature and the precipitated solid is removed by filtration. The filtrate is concentrated to a residue, which is distilled under reduced pressure. The product fractions are collected at 93–106° C. (9–15 mmHg) to give 127 g of the title compound (65%). GC-MS purity is 83–89%, 1HNMR is consistent with expected structure.
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