Br[C:2]1[CH:3]=[C:4]([C:9]([CH3:14])([CH3:13])[C:10](=[O:12])[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8].[C:15]([Cu])#[N:16]>CN1C(=O)CCC1.CCOC(C)=O>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]([CH3:14])([C:10](=[O:12])[CH3:11])[CH3:13])=[CH:3][C:2]=1[C:15]#[N:16]To a solution of 3-(3-bromo-4-fluorophenyl)-3-methylbutan-2-one (13 g, 50 mmol) in NMP (100 mL) was added CuCN (17.9 g, 200 mmol, 4 eq). The mixture was heated 24 h at 160° C. After cooling, the reaction was diluted with EtOAc, washed with 2N HCl (200 mL), satd NaHCO3 (200 mL) and brine (200 mL) successively, dried over MgSO4 and evaporated in vacuo. The residue was purified by column chromatography (Hex/EtOAc=4:1) to give 2-fluoro-5-(2-methyl-3-oxobutan-2-yl)benzonitrile (7.1 g, 69%). 1H NMR (400 MHz, CDCl3) δ 7.56-7.54 (m, 1H), 7.49-7.45 (m, 1H), 7.20 (t, J=8.4 Hz, 1H), 1.96 (s, 3H), 1.50 (s, 6H).
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