[CH:1]([Mg]Br)([CH3:3])[CH3:2].Br[C:7]1[CH:8]=[C:9]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[CH2:10][C:11]#[N:12].Cl>O1CCCC1.[Br-].[Zn+2].[Br-]>[CH:1]([C:7]1[CH:8]=[C:9]([CH2:10][C:11]#[N:12])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17])([CH3:3])[CH3:2]An isopropylmagnesium bromide-0.63M tetrahydrofuran solution (3.2 ml, 2.0 mmol) was added dropwise to a solution of zinc bromide (473 mg, 2.1 mmol) in tetrahydrofuran (2 ml) under ice-cooling. After the mixture was stirred for 15 minutes, the reaction mixture was cooled to −78° C. After 3-bromo-4-methoxybenzyl cyanide (226 mg, 1.0 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II)-dichloromethane adduct (32 mg, 0.04 mmol) were added to the mixture at −78° C., the temperature of the reaction mixture was raised to room temperature and the mixture was further stirred for 5 hours. 1N Hydrochloric acid was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was subjected to silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=8/1-6/1) to give crude (3-isopropyl-4-methoxyphenyl)acetonitrile (158 mg).
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