Borane → 2-(4-Bromophenyl)propan-1-ol
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:12])[C:9](O)=[O:10])=[CH:4][CH:3]=1.B>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH3:12])[CH2:9][OH:10])=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-(4-bromophenyl)propanoic acid (2 g, crude) in tetrahydrofuran (50 mL) was added a solution of borane in tetrahydrofuran (1 mmol/L, 13 mL, 13 mmol) at 0° C. The mixture solution was stirred for 3 hours at 0° C., then worm to room temperature, and quenched by water. The solvent was removed, purified by column chromatography (silica-gel, petroleum:ethyl acetate=5:1) to give 2-(4-bromophenyl)propan-1-ol as a colorless oil (1.8 g, 96%). 1H NMR (300 MHz, CDCl3): δ 1.7.38-7.46 (m, 2H), 7.10-7.13 (m, 2H), 3.72-3.78 (m, 2H), 2.84-2.98 (m, 1H), 1.23-1.27 (m, 3H).
Workup
- customworm to room temperature, and quenched by water
- customThe solvent was removed
- custompurified by column chromatography (silica-gel, petroleum:ethyl acetate=5:1)
Sources & evidence
- ORD record
- ord-f91cf07282c040d3b1e3acfd2d3426a2
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09206128B2
Reaction notes
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