Sodium borohydride → 4-(2,2,2-Trifluoroethyl)phenol

HRID 20063Notes

Reaction equation

HRID 20063 reaction equation
Cl[CH:2]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[C:3]([F:6])([F:5])[F:4].[BH4-].[Na+]>C1COCC1>[F:4][C:3]([F:5])([F:6])[CH2:2][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 114584944-(1-Chloro-2,2,2-trifluoroethyl)phenol

Product 1

HCID 224853604-(2,2,2-Trifluoroethyl)phenol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(1-chloro-2,2,2-trifluoroethyl)phenol (3.60 g, 17.1 mmol) in THF was added sodium borohydride (0.903 ml, 25.6 mmol) in one portion. The reaction was stirred at RT for 18 h, and then quenched with MeOH. The resulting mixture was concentrated and diluted with EtOAc. After washed with water and brine. The organic layer was dried over Na2SO4, filtered and concentrated. The residue was dried in vacuum to afford 4-(2,2,2-trifluoroethyl)phenol as a colorless oil. MS m/z: 175(M−1).

Workup

  1. customquenched with MeOH
  2. concentrationThe resulting mixture was concentrated
  3. additiondiluted with EtOAc
  4. washAfter washed with water and brine
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was dried in vacuum

Sources & evidence

ORD record
ord-003fc360faab496482ebd362427b4fc9
Source dataset
uspto-grants-2010_06
Patent number
US07745484B2

Reaction notes

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