[C:1]([O:5][C:6](=[O:20])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:28])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[C:1]([O:5][C:6]([C:7]1[CH:8]=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([CH2:19][Br:28])=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1)=[O:20])([CH3:4])([CH3:3])[CH3:2]To a solution of tert-Butyl-3-(4-tolyl)benzoate (60 g, 0.22 mol) in CCl4 (800 mL) were added NBS (47.8 g, 0.268 mol) and benzoylperoxide (10 g) and the reaction mixture was refluxed overnight. Cooled to RT and filtered. The filtrate was concentrated to give 4-(3-tert-butoxy carbonyl phenyl)benzyl bromide (65 g, 84%).
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