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

HRID 2207142Notes

Reaction equation

HRID 2207142 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)methanolYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-bromo-4-pyridinecarboxaldehyde 3 (3.0 g, 16.2 mmol) in absolute methanol (40 mL) was added NaBH4 (0.736 g 19.5 mmol) at 0° C. The mixture was stirred at 0° C. for 2 hours under nitrogen. The solvent was then removed under vacuum. Water and ethyl acetate were added and the organic layer was washed with water, dried over Na2SO4 and evaporated under vacuum to afford the compound 4 (3.021 g, 100%) as a white powder.

Workup

  1. customThe solvent was then removed under vacuum
  2. additionWater and ethyl acetate were added
  3. washthe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-bb7c78d3d0b540f092a6812cd00b00eb
Source dataset
uspto-grants-2016_06
Patent number
US09376387B2

Reaction notes

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