Azobisisobutyronitrile → Methyl 3-(4-(bromomethyl)phenyl)-2-propenoate

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A mixture of 3.0 g (17.03 mmol) of methyl 4-methylcinnamate, 3.33 g (18.73 mmol) of N-bromosuccinimide and 60 mg of 2,2'-azobis(2-methylpropionitrile) in 75 ml of carbon tetrachloride was heated to reflux with a heat lamp and stirred rapidly for 30 minutes. The reaction mixture was cooled to room temperature and filtered. The filtrate was evaporated to give the title compound as an oil which crystallized. NMR in CDCl3 (δ units): 3.80 (singlet, 3); 4.48 (singlet, 2); 6.44 and 7.67 (doublets, J=15 Hz, 1); 7.39, 7.49 (doublets, J=7 Hz, 2).

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