Diethyl Ether → 2-(3-Chloro-5-methylphenyl)acetonitrile
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[C-:1]#[N:2].[K+].Br[CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([Cl:13])[CH:7]=1.CCOCC>C(O)C>[Cl:13][C:8]1[CH:7]=[C:6]([CH2:5][C:1]#[N:2])[CH:11]=[C:10]([CH3:12])[CH:9]=1[C-:1]#[N:2].[K+].Br[CH2:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([Cl:13])[CH:7]=1.CCOCC>C(O)C>[Cl:13][C:8]1[CH:7]=[C:6]([CH2:5][C:1]#[N:2])[CH:11]=[C:10]([CH3:12])[CH:9]=1To a flask equipped with additional funnel, was placed potassium cyanide (29.6 g, 0.45 mol) and distilled water (55 ml). The mixture was heated up to 70° C. in an oil bath. With stirring, 1-Bromomethyl-3-chloro-5-methyl-benzene (46) (35 g, 0.16 mol) in ethanol (180 ml) was then dropwise added over 1 hr through the addition funnel. After completion of addition, the mixture was refluxed for 8 hr. After cooling to room temperature, ether was added to the mixture. The mixture was washed with water, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:9)) to afford 20 g (77%) of a pale brown oil. 1H NMR (200 MHz, CDCl3) δ: 2.31 (3H, s), 3.66 (2H, s), 7.02 (1H, s), 7.09 (2H, s).
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