Sodium Bicarbonate → 2-Bromo-5-(dimethoxymethyl)pyridine

HRID 1281143Notes

Reaction equation

HRID 1281143 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][N:3]=1.O.[C:11]1(C)C=CC(S(O)(=O)=O)=CC=1.[C:22](=[O:25])(O)[O-].[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:25][CH3:22])[O:9][CH3:11])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 64252132-Bromo-5-(dimethoxymethyl)pyridineYield 94%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-bromo-5-pyridinecarboxaldehyde (1.02 g, 5.48 mmol) in methanol (100 mL) was added p-toluenesulfonic acid hydrate (1.05 g, 5.53 mmol), and the mixture was heated at reflux for 1.5 h. Diluted aqueous sodium bicarbonate was added, and the mixture was extracted with ethyl acetate twice. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to afford 2-bromo-5-dimethoxymethylpyridine (1.19 g, 94%) as an oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1.5 h
  3. extractionthe mixture was extracted with ethyl acetate twice
  4. washThe organic layer was washed with brine
  5. dry with materialdried on anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3c9b2444ae6742508796e48be196f153
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

Loading…