Sodium borohydride → 4-(2,2,2-Trifluoroethyl)phenol
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customquenched with MeOH
- concentrationThe resulting mixture was concentrated
- additiondiluted with EtOAc
- washAfter washed with water and brine
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was dried in vacuum
Sources & evidence
- ORD record
- ord-003fc360faab496482ebd362427b4fc9
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745484B2
Reaction notes
Loading…