Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][C:4]=1[C:18]([F:21])([F:20])[F:19].[C:22]([Si](C)(C)C)#[N:23].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C(#N)C>[O:10]1[C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=[C:9]1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][C:22]#[N:23])=[C:4]([C:18]([F:21])([F:20])[F:19])[CH:5]=1To a suspension of 2-[4-(bromomethyl)-3-(trifluoromethyl)phenyl]-1,3-benzoxazole (528 mg, 1.5 mmol) and cyanotrimethylsilane (0.30 mL, 2.2 mmol) in acetonitrile (19 mL) was added TBAF (1.0M in THF, 2.2 mL, 2.2 mmol) and the mixture was stirred at rt for 2 h. The solvent was removed in vacuo and the crude was purified by flash chromatography eluting with EtOAc:hexanes (1:9) to afford the desired [4-(1,3-benzoxazol-2-yl)-2-(trifluoromethyl)phenyl]acetonitrile as a colorless solid. 1H NMR (CDCl3, 300 MHz) δ 8.60 (s, 1H), 8.48 (d, 1H), 7.88 (d, 1H), 7.82 (m, 1H), 7.63 (m, 1H), 7.43 (m, 2H), 4.05 (s, 2H). MS (ESI) 303 (M+H)+.
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