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

HRID 1630854Notes

Reaction equation

HRID 1630854 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-38881e00cc914f1e888de6c284016ed7
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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