Sodium Carbonate → 4-Bromo-1-(dimethoxymethyl)-2-fluorobenzene

HRID 1281145Notes

Reaction equation

HRID 1281145 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([F:10])[CH:3]=1.O.[C:12]1(C)C=CC(S(O)(=O)=O)=CC=1.[C:23](=[O:26])([O-])[O-].[Na+].[Na+]>CO>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([O:26][CH3:23])[O:7][CH3:12])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 1435174-Bromo-2-fluorobenzaldehydeHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 184268214-Bromo-1-(dimethoxymethyl)-2-fluorobenzeneYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-bromo-2-fluorobenzaldehyde (3.97 g, 18.8 mmol) in methanol (200 mL) was added p-toluenesulfonic acid monohydrate (357 mg, 1.88 mmol), and the mixture was heated to reflux for 4 h. Aqueous sodium carbonate (1 mol/L; 2 mL) was added, and the mixture was concentrated to a volume of ca. 50 mL and extracted with ether. The organic layer was washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure to afford 4-bromo-1-dimethoxymethyl-2-fluorobenzene (4.56 g, 97%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 4 h
  3. concentrationthe mixture was concentrated to a volume of ca. 50 mL
  4. extractionextracted with ether
  5. washThe organic layer was washed with brine
  6. dry with materialdried on anhydrous sodium sulfate
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-f4ff2335d10d44ceb44087380a47b66f
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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