C[OH:2].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#N)=[C:6]([F:13])[CH:5]=1.O.[C:15]([O-])([O-])=[O:16].[Na+].[Na+]>C(Cl)Cl>[CH3:15][O:16][C:11](=[O:2])[CH2:10][C:7]1[CH:8]=[CH:9][C:4]([Br:3])=[CH:5][C:6]=1[F:13]MeOH (16 mmol, 0.81 ml), TMSCI (20 mmol, 2.13 g) and (4-bromo-2-fluorophenyl) acetonitrile (10 mmol, 2.13 g) were sequentially added to a dry flask under a nitrogen atmosphere at room temperature. The reaction mixture was heated at 50° C. for 4 hours. After being cooled to room temperature, water (20 mmol, 0.36 ml) was added to the mixture, followed by the addition of Na2CO3 (10 mmol, 1.06 g) and CH2Cl2 (10 ml). Drying over MgSO4 and concentrating at low pressure afforded product (0.85 g, 35% yield). 1H NMR (300 MHz, CDCl3) δ: 3.57 (s, 2 H), 3.65 (s, 3H), 7.08 (t, J=8.3 Hz, 1H), 7.16–7.21 (m, 2H).
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