Boron tribromide → 2-Chloro-4-(2,2,2-trifluoroethyl)phenol
Reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=1[Cl:20])C1C=CC=CC=1.B(Br)(Br)Br>ClCCl>[Cl:20][C:10]1[CH:11]=[C:12]([CH2:15][C:16]([F:18])([F:19])[F:17])[CH:13]=[CH:14][C:9]=1[OH:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
1-Benzyloxy-2-chloro-4-(2,2,2-trifluoro-ethyl)benzene (4.0 g, 13.0 mmol) was dissolved in dichloromethane (50 mL) and cooled to −78° C. A solution of boron tribromide (1.0 M in CH2Cl2, 14.3 mL, 14.3 mmol) was added. The reaction mixture was warmed to 0° C., diluted with dichloromethane and washed with brine. After removal of solvent, the residue was chromatographed on silica gel eluting with 9:1 hexane:ethyl acetate to give the title compound.
Workup
- temperatureThe reaction mixture was warmed to 0° C.
- washwashed with brine
- customAfter removal of solvent
- customthe residue was chromatographed on silica gel eluting with 9:1 hexane
Sources & evidence
- ORD record
- ord-0711597848bf4024965615475c261c00
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07524882B2
Reaction notes
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