[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8]Br)[C:3]=1[F:10].C[Si]([C:15]#[N:16])(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CC#N>[Cl:1][C:2]1[C:3]([F:10])=[C:4]([CH2:8][C:15]#[N:16])[CH:5]=[CH:6][CH:7]=1To a solution of 1-chloro-3-bromomethyl-2-fluoro-benzene (2.22 g, 10 mmol) in CH3CN (30 mL) was added trimethylsilyl cyanide (1.5 mL) and TBAF (1M in THF, 12 mmol, 12 mL). The resulting reaction mixture was heated at reflux temperature for 30 min. After cooling to room temperature, the volatiles were evaporated under reduced pressure. The residue was partitioned between EtOAc and water. The organic layer was then washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography to give the title compound (1.48 g, 88%). MS: 170.1 (M+H)+.
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