O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])=[N:7][CH:8]=1.O=S(Cl)[Cl:19]>O1CCOCC1.CCOCC.[Cl-].[Cl-].[Zn+2]>[Cl:19][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])=[N:7][CH:8]=1To a cooled (0° C.), stirred solution of 2-[5-(hydroxymethyl)pyridin-2-yl]benzonitrile (4.3 g, 0.020 mol) and ZnCl2 (0.09 g, 0.61 mmol) in p-dioxane (40 mL) was added SOCl2 (1.50 mL, 0.020 mol) dropwise. The mixture was stirred at room temperature for 18 h, diluted with ether, washed with water and brine, dried (MgSO4), and concentrated to give 4.30 g (92%) of product as a brown solid, mp 97°-98° C.
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