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

HRID 2277604Notes

Reaction equation

HRID 2277604 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]([CH:10]=[O:11])[CH:7]=[N:8][CH:9]=1>CO.CCOC(C)=O>[Br:3][C:4]1[CH:5]=[C:6]([CH2:10][OH:11])[CH:7]=[N:8][CH:9]=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

Sodium borohydride (2.2 g, 59.1 mmol) was added to a suspension of 5-bromo-pyridine-3-carbaldehyde (10.0 g, 53.7 mmol) in MeOH (100 mL) at 0° C. The mixture was stirred at 0° C. for 1 hour before it was quenched by the addition of water (5.0 mL). Evaporation of solvents afforded a light yellowish oil which was re-dissolved in EtOAc and washed with water. 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 by the addition of water (5.0 mL)
  2. customEvaporation of solvents
  3. customafforded a light yellowish oil which
  4. washwashed with water
  5. customThe organic layer was dried over anhy
  6. filtrationNa2SO4, filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2f240ac9da77489d95b8591c5ee8233a
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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