C(N(CC)CC)C.C(O)(C)(C)C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=1.Br[CH2:24][C:25](=[O:28])[CH2:26][CH3:27]>[Cl-].[Zn+2].[Cl-].C1C=CC=CC=1>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH2:21][CH2:24][C:25](=[O:28])[CH2:26][CH3:27])=[CH:16][CH:15]=1
Anhydrous zinc chloride (3.71 g, 27.2 mmol) was placed into a round bottom flask and dried by melting under vacuum at 250-350° C. for 15 minutes. After cooling under vacuum to room temperature, benzene (15 ml.), triethylamine (2.7 ml, 19.42 mmol) and tert-butanol (1.83 ml, 19.42 mmol) were successively added. The mixture was stirred until zinc chloride was fully dissolved (approx. 2 hour) and 1-(4-chlorophenyl)ethan-1-one (3.0 g, 19.42 mmol) and 1-bromobutan-2-one (2.05 g, 13.6 mmol) were successively added. The mixture was stirred for 1 hour and allowed to stand for 4 days at room temperature, and thereafter quenched with 5% aq. sulfuric acid. The organic layer was separated, washed with water (2×50 ml), brine (1×25 ml), dried over anhydrous sodium sulfate and the solvent evaporated off. The crude product was purified by column chromatography over silica gel (100-200 mesh) using chloroform as eluent to give 2.30 g (75.63%) of the title compound.
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