[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[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:10]=[CH:9][C:5]([C:6]([C:14]2[CH:15]=[CH:16][C:11]([O:17][CH3:18])=[CH:12][CH:13]=2)=[O:7])=[CH:4][CH:3]=1To a cooled (0° C.) mixture of 4-bromobenzoyl chloride, 1-1-a, (25 g, 0.114 mol) and anisole (15.5 g, 0.143 mol) in DCM (500 ml) was added AlCl3 (19 g, 0.143 mol) portion wise with stirring under N2. The resulting reaction mixture was allowed to stir at r.t for 16 h. The reaction mixture was poured into 20% HCl (500 ml) and the solution stirred for 1 h. After stirring, the resulting solution was allowed to separate into phase layers. The aqueous layer was collected and further extracted with DCM (3×250 ml). The combined organic layer was washed with water (200 ml), brine (200 ml), dried (Na2SO24), filtered and concentrated under reduced pressure to yield 30 g of a white solid, 1-1-b. 1H NMR (300 MHZ, CDCl3): 3.91 (s, 3H), 6.99 (d, 2H), 7.65 (s, 4H), 7.82 (d, 2H).
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