Sodium Bicarbonate → HCID 22566648, compound

HRID 1281134Notes

Reaction equation

HRID 1281134 reaction equation
[Br:1][C:2]1[O:6][C:5]([CH:7]=[O:8])=[CH:4][CH:3]=1.O.[C:10]1(C)C=CC(S(O)(=O)=O)=CC=1.[C:21](=[O:24])(O)[O-].[Na+]>CO>[Br:1][C:2]1[O:6][C:5]([CH:7]([O:24][CH3:21])[O:8][CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 6003285-Bromofuran-2-carbaldehyde

Product 1

HCID 22566648HCID 22566648, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-bromofuran-2-carboxaldehyde (350 mg, 2.00 mmol) in methanol (15 mL) was added p-toluenesulfonic acid monohydrate (38 mg, 0.20 mmol), and the mixture was heated at reflux for 2 h. The reaction mixture was cooled to room temperature, and aqueous sodium bicarbonate was added. The mixture was extracted with ether, and the organic layer was washed with brine, dried on anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to afford 2-bromo-5-dimethoxymethylfuran (274 mg, 62%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 2 h
  3. extractionThe mixture was extracted with ether
  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-39fca10e32d7484d88eb80f46f43646d
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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