Dimethyl Sulfate → 3-Bromo-4,5-dimethoxybenzaldehyde

HRID 1057848Notes

Reaction equation

HRID 1057848 reaction equation
[Br:1][C:2]1[C:3]([OH:12])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:13](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O>CC(C)=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:9]=[C:6]([CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[O:12][CH3:13])[CH:7]=[O:8]

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 180995-Bromovanillin

Product 1

HCID 813793-Bromo-4,5-dimethoxybenzaldehydeYield 89%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-bromovanillin (2.00 g, 8.65 mmol) in acetone (50 mL) was added potassium carbonate (1.4 g, 10.38 mmol) and dimethylsulfate (1 mL, 10.38 mmol). The solution was stirred at room temperature for 16 hours. The reaction mixture was diluted with ethyl acetate and the organic layer was washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated to afford 1.88 g of 3-bromo-4,5-dimethoxybenzaldehyde (89%).

Workup

  1. washthe organic layer was washed successively with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-79634e0cabe84ec3b670c3d45ba993b4
Source dataset
uspto-grants-2003_02
Patent number
US06515003B1

Reaction notes

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