Boron tribromide → 4-Piperidin-1-yl-3-trifluoromethyl-phenol
Reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[C:5]([C:15]([F:18])([F:17])[F:16])[CH:4]=1.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>C(Cl)Cl>[N:9]1([C:6]2[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][C:5]=2[C:15]([F:16])([F:17])[F:18])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of crude 1-(4-Methoxy-2-trifluoromethyl-phenyl)-piperidine in dry DCM (3 mL) cooled to −78° C. is added BBr3 (1M in DCM, 3 eq., 1.2 mL). Following this addition, the cooling bath is removed and the reaction is stirred at 25° C. for 12 hours. Upon completion, the reaction is cooled in an ice bath, and water is added dropwise. The quenched reaction is basified to pH=8 by the slow addition of 10% NaHCO3 (aq). The reaction mixture is diluted with DCM and washed with H2O followed by saturated aqueous NaCl. The organic solution is dried over Na2SO4. After concentration, the residue is purified by silica gel chromatography (3:1 hexanes/EtOAc) to give 4-Piperidin-1-yl-3-trifluoromethyl-phenol. [MS: (ES+) 246.1 (M+1)+].
Workup
- additionthis addition
- customthe cooling bath is removed
- temperatureUpon completion, the reaction is cooled in an ice bath
- additionwater is added dropwise
- customThe quenched reaction
- washwashed with H2O
- dry with materialThe organic solution is dried over Na2SO4
- concentrationAfter concentration
- customthe residue is purified by silica gel chromatography (3:1 hexanes/EtOAc)
Sources & evidence
- ORD record
- ord-dc7768751a3f45d1aac363a7059fdbf2
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07572811B2
Reaction notes
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