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

HRID 1765422Notes

Reaction equation

HRID 1765422 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

The intermediate 3-bromo-4,5-dimethoxybenzaldehyde was prepared as follows: 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. customThe intermediate 3-bromo-4,5-dimethoxybenzaldehyde was prepared
  2. washthe organic layer was washed successively with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-36d33634e95f4c4fb8051c9c30cbc129
Source dataset
uspto-grants-2007_06
Patent number
US07226940B2

Reaction notes

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