[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH3:14])[CH:11]=[CH:12][CH:13]=2)=[O:7])=[CH:4][CH:3]=1.[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[CH2:14][Br:17])=[O:7])=[CH:15][CH:16]=1A mixture of 3-(4-chlorobenzoyl)toluene (5.48 g, 23.7 mmol) and dibenzoylperoxide (100 mg, 0.413 mmol) in carbon tetrachloride (45 ml) was treated with N-bromosuccinimide (4.65 g, 26.7 mmol) and refluxed 2.5 hours. The mixture was filtered while hot and slowly cooled to ambient temperature. The precipitate was collected by filtration, washed twice with carbon tetrachloride, and dried under vacuum to provide 4.2 g (57%) of 3-(4-chlorobenzoyl)benzyl bromide, m.p. 123°-125° C.
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