3-Bromopyridine-4-carboxaldehyde → (3-Bromopyridin-4-yl)methanol
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH:8]=[O:9].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][OH:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-bromo-pyridine-4-carbaldehyde (0.500 g, 2.68 mmol) in MeOH (5 mL) at 0° C. is added sodium borohydride (0.122 g, 3.22 mmol). The mixture is stirred at room temperature for 1 h followed by removal of the solvent in vacuo. The residue is redissolved in DCM and washed with water twice. The organic layer is dried over sodium sulfate and concentrated in vacuo to afford (3-bromo-pyridin-4-yl)-methanol as a yellow oil. MS (ESI) m/z 189.9 (M+H)+
Workup
- customfollowed by removal of the solvent in vacuo
- dissolutionThe residue is redissolved in DCM
- washwashed with water twice
- dry with materialThe organic layer is dried over sodium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-196e5af2399b48d5b099b41a5f155237
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242963B2
Reaction notes
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