3-Bromobenzaldehyde → 3-Bromobenzyl alcohol
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[BH4-].[Na+]>CCO>[Br:1][C:2]1[CH:3]=[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-bromobenzaldehyde (114.8 g, 620.4 mmol) in EtOH (650 mL), NaBH4 (7.1 g, 186.1 mmol) was added in several portions at 25° C. Then the mixture was stirred for 1 h at room temperature. The reaction was quenched with water (200 mL). After removing EtOH, the residue was dissolved in AcOEt (500 mL), and filtered. The filter was washed with water (150 mL), brine (150 mL), and dried over Na2SO4. After removing the solvent, 115.8 g of the title compound was obtained (Yield: 99.8%).
Workup
- customThe reaction was quenched with water (200 mL)
- customAfter removing EtOH
- dissolutionthe residue was dissolved in AcOEt (500 mL)
- filtrationfiltered
- washThe filter was washed with water (150 mL), brine (150 mL)
- dry with materialdried over Na2SO4
- customAfter removing the solvent
Sources & evidence
- ORD record
- ord-fd6be139b26d4c7a842b1521f0a2edb7
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08067408B2
Reaction notes
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