Potassium Carbonate → 3-(4-Bromophenyl)propan-1-ol
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.O1CCCC1.B.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-(4-bromophenyl)propionic acid (1.0 g) in tetra hydrofuran (15 mL) was added borane tetra hydrofuran complex (1.0 mol/L tetra hydrofuran solution, 6.55 mL) under ice-cooling, and the mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 20% aqueous potassium carbonate solution under ice-cooling, and the resulting mixture was extracted with ethylacetate. The extract was washed with brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give 3-(4-bromophenyl)propanol (0.93 g). The title compound was prepared in a similar manner to that described in Reference Example 55 using this material instead of 2-(4-bromo-phenyl)ethanol.
Workup
- temperaturecooling
- temperaturecooling
- extractionthe resulting mixture was extracted with ethylacetate
- washThe extract was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-c421cc4fe4ea460f8e8ab435f6d671b9
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07750145B2
Reaction notes
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