[CH3:1][CH:2]([C:8]([CH3:13])([CH3:12])[CH:9]=[CH:10][CH3:11])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:14]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:14][CH2:11][CH:10]=[CH:9][C:8]([CH3:13])([CH3:12])[CH:2]([CH3:1])[C:3]([O:5][CH2:6][CH3:7])=[O:4]A mixture of 920 mg (5 mmoles) of ethyl 2,3,3-trimethyl-4-hexenoate, 10 ml of carbon tetrachloride, 107 mg (6 mmoles) of N-bromosuccinimide, and 50 mg of benzoyl peroxide was heated under reflux for about two hours. The insoluble succinimide was removed by filtration. The filtrate was washed successively with saturated aqueous sodium bicarbonate solution and water, then dried over magnesium sulfate. The dried solution was distilled to give 1.14 g (86% yield) of ethyl 6-bromo-2,3,3-trimethyl-4-hexenoate, b.p. 80°-81°/0.8 mm.
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