[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([O:9][C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:11]=2)=[C:5]([F:21])[CH:4]=1)=[CH2:2].B1C2CCCC1CCC2.[OH-:31].[Na+].OO>C1COCC1>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([O:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:1][CH2:2][OH:31])=[CH:4][C:5]=2[F:21])=[CH:11][C:12]=1[C:17]([F:20])([F:18])[F:19]
To a solution of 4-chloro-3-(trifluoromethyl)phenyl 4-ethenyl-2-fluorophenyl ether (4.0 g, 12.63 mmol) in THF (13 mL) was added dropwise 9-BBN (50.5 mL, 25.3 mmol) at 0° C. The reaction mixture was stirred at room temperature for overnight, then mixed with NaOH (25.3 mL, 76 mmol) and H2O2 (7.74 mL, 76 mmol). The mixture was stirred at 55° C. for 4 h, quenched by Na2SO3, and extracted with EA (100 mL×3). Organic phases were collected, combined, dried with anhydrous Na2SO4, and concentrated to provide the title compound (4.02 g, 95% yield). LCMS: rt=4.6 min, [M+H+]=334
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