[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][CH3:10].[CH2:11]([C:13]1[CH:21]=[CH:20][C:16]([C:17](Cl)=[O:18])=[CH:15][CH:14]=1)[CH3:12].[Cl-].[Cl-].[Cl-].[Al+3]>ClCCl>[Br:1][C:2]1[C:3]([O:9][CH3:10])=[CH:4][C:5]([Cl:8])=[C:6]([C:17]([C:16]2[CH:20]=[CH:21][C:13]([CH2:11][CH3:12])=[CH:14][CH:15]=2)=[O:18])[CH:7]=1To a solution of 1-bromo-4-chloro-2-methoxybenzene (5.1 g, 23 mmol) and 4-ethylbenzoyl chloride (4.1 g, 24 mmol) in 15 mL of anhydrous dichloromethane (DCM) was added aluminum trichloride (3.2 g, 24 mmol). The mixture was stirred at room temperature for 1 hour, followed by heating at reflux for 18 hours. The mixture was poured into 100 mL of ice-cold water and the organic layer was isolated. The aqueous solution was extracted with 25 mL DCM. The combined organic extracts were washed with brine (25 mL), dried (Na2SO4), filtered, and evaporated. Recrystallization from petroleum ether gave the intermediate (5-bromo-2-chloro-4-methoxyphenyl)(4-ethylphenyl)methanone 21 (5.6 g, 69%).
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