[CH3:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:5].[Br:15]Br.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.CCCCCC.C(OCC)(=O)C>ClC1C=CC=CC=1>[Br:15][CH2:1][C:2]1[CH:14]=[CH:13][CH:12]=[CH:11][C:3]=1[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:5]To a solution of ethyl 2-methylbenzoylformate (10 g) in chlorobenzene (50 ml) were added a solution of bromine (10 g) in chlorobenzene (20 ml) and a suspension of 25%-hydrous benzoyl peroxide (1 g) in chlorobenzene (10 ml) over 2 hours and the mixture was heated under reflux for 1 hour. The reaction mixture was cooled with ice-water and filtered through a pad of celite. The filtrate was concentrated under reduced pressure to give a yellow oil. The oil was subjected to silica gel column chromatography (eluent: hexane/ethyl acetate=20/1) to give the desired ethyl 2-(bromomethyl)benzoylformate (1.4 g, yield: 10%).
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