Water → 1-Fluoro-2-hydroxy-2-phenylpropane

HRID 1781124Notes

Reaction equation

HRID 1781124 reaction equation
[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]

Participants

6

Reactant 3

HCID 962WaterHCID 7407Alpha-MethylstyreneHCID 27373291-Fluoro-4-hydroxy-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

Product 1

HCID 104418951-Fluoro-2-hydroxy-2-phenylpropaneYield 71.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

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-hydroxy2-phenylpropane.

Workup

  1. filtrationfiltered through anhydrous MgSO4
  2. customevaporated

Sources & evidence

ORD record
ord-3db210e326114ffbb72dd55072cee33b
Source dataset
uspto-grants-1997_05
Patent number
US05631372

Reaction notes

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