[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].[C:11]1([O:17][CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Al+3].[Cl-].[Cl-].[Cl-].Cl>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:5]([C:14]2[CH:15]=[CH:16][C:11]([O:17][CH3:18])=[CH:12][CH:13]=2)=[O:6])[CH:8]=[CH:9][CH:10]=1To a cooled (0° C.) mixture of 3-bromobenzoyl chloride (5-a, 178 g, 0.82 mol) and anisole (110 g, 1.03 mol) in DCM (2.0 L) was added AlCl3 (138 g, 1.03 mol) portion wise with stirring under N2. The resulting reaction mixture was allowed to stir at r.t overnight. The reaction mixture was poured into 20% HCl (1500 ml), stirred for 1 h, and layers were separated. The aqueous layer was further extracted with DCM (2×750 ml). The combined organic layer was washed with water, brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was washed with hexane to afford the product, 5-b, (190 g, 84%).
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