[Al+3].[Cl-].[Cl-].[Cl-].[Br:5][CH2:6][C:7](Br)=[O:8].[CH3:10][O:11][C:12]1[CH:17]=[C:16]([CH3:18])[CH:15]=[C:14]([CH3:19])[CH:13]=1>C(Cl)Cl>[Br:5][CH2:6][C:7]([C:13]1[C:14]([CH3:19])=[CH:15][C:16]([CH3:18])=[CH:17][C:12]=1[O:11][CH3:10])=[O:8].[Br:5][CH2:6][C:7]([C:15]1[C:16]([CH3:18])=[CH:17][C:12]([O:11][CH3:10])=[CH:13][C:14]=1[CH3:19])=[O:8]
To a mixture of AlCl3 (2.0 g, 14.7 mmol) in CH2Cl2 (12 mL) was added a solution of 2-bromoacetyl bromide (3.0 g, 14.9 mmol) in CH2Cl2 (2 mL) at 0° C. Then, a solution of 1-methoxy-3,5-dimethylbenzene (2.0 g, 14.7 mmol) in CH2Cl2 (2 mL) was added dropwise. The whole mixture was stirred for 1.5 h at 0 to 5° C. After that, the mixture was poured into ice water (100 g). The mixture was extracted with CH2Cl2 (3×30 mL). The combined organic phases were dried over anhydrous Na2SO4. After filtration, the solvent was removed in vacuo and the residue was purified by silica gel column (hexane/EtOAc=40/1 to 25/1) to afford 2-bromo-1-(2-methoxy-4,6-dimethylphenyl)ethanone (1.20 g, 31.7%) and 2-bromo-1-(4-methoxy-2,6-dimethylphenyl) ethanone (250 mg, 6.6%).
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