Sodium borohydride → 1-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethanol
Reaction equation
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].[BH4-].[Na+]>CO>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH:10]([OH:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1-(3-bromo-5-chloro-2-methoxy-4-methylphenyl)ethanone (23 g, 83 mmol) in methanol (200 mL) was added sodium tetrahydroborate (5.0 g, 130 mmol) at 0° C. The mixture was stirred at 0° C. for 1 hour and quenched with water (10 mL). The resulting mixture was concentrated under reduced pressure to about 30 mL. The residue was diluted with ethyl acetate, washed with water and brine, dried over MgSO4, filtered and evaporated to yield the desired product. LCMS calculated for C10H11BrClO (M−OH)+: m/z=261.0, 263.0. found: 261.0, 263.0.
Workup
- customquenched with water (10 mL)
- concentrationThe resulting mixture was concentrated under reduced pressure to about 30 mL
- additionThe residue was diluted with ethyl acetate
- washwashed with water and brine
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-0f994c4e92c6429289fc095f946fb1fd
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096600B2
Reaction notes
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