[Br:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl.[W].C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:11][Br:12])[C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1A mixture of 5-bromo-7-methyl-benzofuran (1.01 g), N-bromosuccinimide (1.04 g) and benzoyl peroxide (58 mg) in carbon tetrachloride (10 ml) was heated at reflux for 4 h under a 250 W tungsten lamp. A further portion of benzoyl peroxide (58 mg) was added and heating and irradiation continued for a total of 9 h. The reaction mixture was allowed to cool, diluted with chloroform (30 ml) and washed with 2N sodium hydroxide (40 ml) and then brine (40 ml). The organic phase was dried, filtered and the filtrate evaporated in vacuo to give the title compound as a brown oil (1.57 g).
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