[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH:17]=[CH2:18])=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:19]([F:22])([F:21])[F:20].B1C2CCCC1CCC2.[OH2:32].[OH-].[Na+].OO>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][OH:32])=[CH:13][C:10]=2[C:11]#[N:12])=[CH:4][C:3]=1[C:19]([F:20])([F:21])[F:22]To the solution of 2-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}-5-ethenylbenzonitrile (2.0 g, 6.18 mmol) in dry THF (14 mL), was added 9-BBN (18 mL, 9.00 mmol) at 0° C. The mixture was stirred at room temperature overnight. Water (1.113 mL, 61.8 mmol), aq. NaOH (12.36 mL, 37.1 mmol), and 30% H2O2 (3.16 mL, 30.9 mmol) were added then. The reaction mixture was heated at 55° C. for 4 h. Then THF was removed under reduced pressure, and the residue was diluted with EA. The organic layer was washed with water and brine, dried over anhydrous Na2SO4 and concentrated and purified by flash chromatography to afford the title compound (1.0 g, 2.93 mmol, 47.4% yield).
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