Methanol → 2-(3-bromo-4-methoxyphenyl)ethanol
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11](O)=[O:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].S(C)C.CO>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of [3-bromo-4-(methyloxy)phenyl]acetic acid (10.0 g, 40.8 mmol) in anhydrous THF (50 mL) was added BH3.(CH3)2S (5.3 mL, 53 mmol) dropwise at 0° C. The resulting mixture was stirred at 0° C. for 3 h. The mixture was then treated with MeOH until gas evolution subsided, and then concentrated under reduced pressure. The residue was then partitioned between water and EtOAc. The organic layers were washed with brine, dried over Na2SO4 and concentrated to give crude 2-[3-bromo-4-(methyloxy)phenyl]ethanol, which was used without further purification for the next step.
Workup
- customdropwise at 0° C
- concentrationconcentrated under reduced pressure
- customThe residue was then partitioned between water and EtOAc
- washThe organic layers were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1ff685eba206469291f3b2aafe69956f
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018211B2
Reaction notes
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