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

HRID 2277711Notes

Reaction equation

HRID 2277711 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[O:9])[CH:5]=[N:6][CH:7]=1.[BH4-].[Na+]>CO.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH2:8][OH:9])[CH:5]=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2784733(5-Bromo-3-pyridinyl)methanolYield 95.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 5-bromo-pyridine-3-carbaldehyde (10.0 g, 53.7 mmol) in MeOH (100 mL) was added sodium borohydride (2.2 g, 59.1 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour before it was quenched with water (5.0 mL). Evaporation of solvents afforded light yellowish oil which was re-dissolved in EtOAc and washed with brine. The organic layer was dried over anhy. Na2SO4, filtered and concentrated in vacuo to give the title compound (9.6 g, 95%) as colorless oil. MS: 188.0 & 190.0 (M+H+).

Workup

  1. customwas quenched with water (5.0 mL)
  2. customEvaporation of solvents
  3. customafforded light yellowish oil which
  4. washwashed with brine
  5. customThe organic layer was dried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f07b7a68adba43a794913993907bb542
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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