Sodium borohydride → (3-Bromo-2-ethylphenyl)methanol
Reaction equation
[Br:1][C:2]1[C:3]([CH2:10][CH3:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[BH4-].[Na+]>CO>[Br:1][C:2]1[C:3]([CH2:10][CH3:11])=[C:4]([CH2:5][OH:6])[CH:7]=[CH:8][CH:9]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-bromo-2-ethylbenzaldehyde (5 g, 23.47 mmol) in Methanol (50 mL) was added NaBH4 (1.776 g, 46.9 mmol) at 0° C. The reaction solution was stirred at room temperature for 2 hours. The solvent was removed in vacuo and the residue was dissolved in ethyl acetate, washed with water, dried over sodium sulphate, concentrated and purified by ISCO column chromatography to afford (3-bromo-2-ethylphenyl)methanol (D133) (3 g) as an oil. MS (ES): C9H11BrO requires 213.99. found 197.0 (M+H+-18).
Workup
- customThe solvent was removed in vacuo
- dissolutionthe residue was dissolved in ethyl acetate
- washwashed with water
- dry with materialdried over sodium sulphate
- concentrationconcentrated
- custompurified by ISCO column chromatography
Sources & evidence
- ORD record
- ord-52b5562d3a404dc19a1d7688650a783c
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08389508B2
Reaction notes
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