[H-].[Na+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]Br.Cl>CS(C)=O.CS(C)=O.CCOCC.O>[C:3]1([C:9]2([C:10]#[N:11])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1To a suspension of NaH (42.7 g, 1067.0 mmol, 60%) in dimethyl sulfoxide (600.0 mL) were added drop-wise a mixture of phenylacetonitrile (50.0 g, 426.8 mmol) and 1,5-dibromopentane (58.1 mL, 426.8 mmol) dissolved in dimethyl sulfoxide:ether (1:1) (200.0 mL) at 0° C. and the reaction mixture was stirred at this temperature for 2 h. After completion of the reaction, water and a 10% HCl solution were added to the mixture and the mixture was extracted with ethyl acetate. The combined organic layer was then washed with water and brine and dried over sodium sulfate and concentrated under reduced pressure to obtain a crude product. This crude product was then purified by normal silica gel column chromatography (using hexane) to get 1-phenyl-cyclohexanecarbonitrile (249) (52.0 g, 65.76%) as a colorless oil.
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