Br[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[Cl:14])[N:6]=[C:5]([C:15]([F:18])([F:17])[F:16])[CH:4]=1.[C-:19]#[N:20].[Na+]>CN(C=O)C.CCOCC.O>[Cl:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[N:7]1[C:3]([CH2:2][C:19]#[N:20])=[CH:4][C:5]([C:15]([F:18])([F:17])[F:16])=[N:6]1Into a 250 mL flask was weighed 11.3 g of 5-(bromomethyl)-1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazole (33 mmol) which was then dissolved in 40 mL of dry DMF. The resulting solution was treated with 2.5 g of sodium cyanide (52 mmol). The resulting suspension was heated to 50° C. After 4 hours at 50° C., heating was discontinued and the reaction was allowed to cool to room temperature. After standing at room temperature for 2 days the reaction was diluted with ether and H2O. The layers were separated and the aqueous layer was extracted with ether (4×). The combined organic layers were washed with H2O (3×), then brine (2×), dried (Na2SO4), filtered and concentrated in vacuo to afford crude 2-(1-(2-chlorophenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)acetonitrile as a red oil, yield 8.2 g (86%), 1H NMR (400 MHz, CDCl3): δ 7.62-7.46 (m, 4H), 6.82 (s, 1H), 3.9-3.4 (broad hump, 2H).
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