3-Bromopyridine-4-carboxaldehyde → (3-Bromopyridin-4-yl)methanol

HRID 593584Notes

Reaction equation

HRID 593584 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

HCID 27629973-Bromopyridine-4-carboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 46840038(3-Bromopyridin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. customfollowed by removal of the solvent in vacuo
  2. dissolutionThe residue is redissolved in DCM
  3. washwashed with water twice
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-196e5af2399b48d5b099b41a5f155237
Source dataset
uspto-grants-2016_01
Patent number
US09242963B2

Reaction notes

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