[F:1][C:2]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[CH:6][C:3]=1[C:4]#[N:5].[CH2:12]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]([O:25][Si](C)(C)C)=[CH2:24])[CH:13]([CH3:15])[CH3:14]>ClCCl.[Ti](Cl)(Cl)(Cl)Cl>[F:1][C:2]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:24]/[C:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:25])=[CH:6][C:3]=1[C:4]#[N:5]To a solution of commercially available 2-fluoro-5-formylbenzonitrile (2.49 g, 10 mmol) in dichloromethane (40 mL) was added (1-(2-isobutoxyphenyl)vinyloxy)trimethylsilane (1.49 g, 10 mmol), followed by titanium tetrachloride (1.5 eq). The reaction was stirred at room temperature for 5 hours and then heated at 40° C. for overnight. The reaction was cooled and quenched with 1 N HCl (40 mL). The mixture was stirred for 2 hours and diluted with dichloromethane/water. The organic layer was separated, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by the chromatography to give (E)-2-fluoro-5-(3-(2-isobutoxyphenyl)-3-oxoprop-1-enyl)benzonitrile as a white solid (1.60 g, 50% yield). 1H NMR (400 MHz, CDCl3): δ 7.88-7.75 (m, 2H), 7.70 (d, 1H), 7.57 (d, 1H), 7.54-7.45 (m, 2H), 7.28 (d, 1H), 7.08-6.98 (m, 2H), 3.84 (d, 2H), 2.17-2.03 (m, 1H), 1.00 (d, 6H). MS (EI) for C20H18FNO2: 268 (MH+).
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