[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[CH2:3].[OH2:10].[F:11][B-](F)(F)F.F[B-](F)(F)F.O[N+]12CC[N+](F)(CC1)CC2>C(#N)C.CCOCC>[F:11][CH2:3][C:2]([OH:10])([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:1]To a solution of alpha-methylstyrene (0.13 mL, 1 mmole) and water (0.02 mL, 1.1 mmole) in acetonitrile (10 mL) was added 1-hydroxyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (330 mg, 1.02 mmole 1.02 equ.) and the reaction stirred at room temperature for 24 h. The mixture was diluted with ether (2 mL), filtered through anhydrous MgSO4, and evaporated to afford 110 mg (71% yield) of 1-fluoro-2-hydroxy-2-phenylpropane.
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