5-Bromo-3-pyridinecarboxaldehyde → (5-Bromo-3-pyridinyl)methanol

HRID 1712915Notes

Reaction equation

HRID 1712915 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].[BH4-].[Na+]>CCO>[Br:1][C:2]1[CH:9]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2784733(5-Bromo-3-pyridinyl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-bromonicotinaldehyde (4.36 g, 23.4 mmol) in EtOH (90 mL) at 0° C. was added sodium borohydride (4.4 g, 120 mmol). The reaction mixture was allowed to stir and warm to rt overnight and then quenched by the addition of saturated aq. NH4Cl. The mixture was concentrated to small volume and the residue was extracted with EtOAc. The organic solutions were combined, dried over Na2SO4, filtered and concentrated to give (4.21 g, 86%) as a light yellow oil which was used without purification. LCMS: (FA) ES+ 186.0.

Workup

  1. customquenched by the addition of saturated aq. NH4Cl
  2. concentrationThe mixture was concentrated to small volume
  3. extractionthe residue was extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give (4.21 g, 86%) as a light yellow oil which
  8. customwas used without purification

Sources & evidence

ORD record
ord-940606cd298f46e5a979149827797f46
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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