CCOCC.C1COCC1.[F:11][C:12]([F:20])([F:19])[C:13](=[O:18])[CH:14]=[C:15]([CH3:17])[CH3:16].[F:21][C:22]1[CH:27]=[CH:26][C:25]([Mg]Br)=[CH:24][CH:23]=1>[Cu]I.CCOCC>[F:11][C:12]([F:20])([F:19])[C:13](=[O:18])[CH2:14][C:15]([C:25]1[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=1)([CH3:17])[CH3:16]To a 2 M ether/THF solution of 1,1,1-trifluoro-4-methylpent-3-en-2-one was added 3.8 g of copper (I) iodide and 10 mL of a 2 M ether solution of 4-fluorophenylmagnesium bromide at 0° C. The mixture was warmed to room temperature and stirred for 2 hours. The reaction was quenched with saturated aqueous NH4Cl, and extracted three times with EtOAc. The combined organic layers were washed with water, brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash chromatography to yield 460 mg of 1,1,1-trifluoro-4-(4-fluorophenyl)-4-methylpentan-2-one.
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