2,2,2,4'-Tetrafluoroacetophenone → 2,2,2-Trifluoro-1-(4-fluorophenyl)ethanol

HRID 1696054Notes

Reaction equation

HRID 1696054 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=[O:4].[BH4-].[Na+]>CO>[F:13][C:2]([F:1])([F:12])[CH:3]([C:5]1[CH:6]=[CH:7][C:8]([F:11])=[CH:9][CH:10]=1)[OH:4]

Participants

4

Reactant 2

HCID 695642,2,2,4'-TetrafluoroacetophenoneHCID 4311764Sodium borohydride

Product 1

HCID 111482462,2,2-Trifluoro-1-(4-fluorophenyl)ethanolYield 111.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 2,2,2,4′-tetrafluoroacetophenone (10 g, 52.1 mmol) in methanol (50 mL) was added NaBH4 (0.98 g, 26.5 mmol) at 0° C. After stirring at 25° C. for 2 h, the reaction mixture was quenched by adding 1N HCl (100 mL) and then extracted with ethyl ether. The ether extract was washed with brine, dried with MgSO4, and concentrated to give 2,2,2-trifluoro-1-(4-fluorophenyl)ethanol (11.32 g) which was used in next step without further purification.

Workup

  1. customthe reaction mixture was quenched
  2. additionby adding 1N HCl (100 mL)
  3. extractionextracted with ethyl ether
  4. extractionThe ether extract
  5. washwas washed with brine
  6. dry with materialdried with MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-322db311a21e41adb15faed8296395c1
Source dataset
uspto-grants-2012_04
Patent number
US08163735B2

Reaction notes

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