[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:3][CH:2]=1.[Br:14]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[Br:14][CH2:13][C:1]1[CH:6]=[CH:5][C:4]([O:7][CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:3][CH:2]=1To a solution of the methyl 2-(p-tolyloxy)acetate (3.10 g, 17.2 mmol) in carbon tetrachloride (60 mL) was added N-bromosuccinimide (3.57 g, 20 mmol) followed by benzoyl peroxide (463 mg, 1.9 mmol). The resulting solution was heated at reflux overnight, and then diluted with methylene chloride. The mixture was washed with brine, dried on MgSO4, and concentrated. The resulting colorless oil was purified by chromatography on silica gel (Hexane/ethyl acetate 9/1) to afford a colorless oil (2.5 g, 56%).
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