Dimethyl Sulfate → 2-Bromo-3,4-dimethoxybenzaldehyde

HRID 1582381Notes

Reaction equation

HRID 1582381 reaction equation
[Br:1][C:2]1[C:9]([OH:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:13]([O-])([O-])=O.[K+].[K+].COS(OC)(=O)=O>CN(C=O)C>[Br:1][C:2]1[C:9]([O:10][CH3:13])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 2240112-Bromoisovanillin

Product 1

HCID 6185382-Bromo-3,4-dimethoxybenzaldehydeYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-10 °C

Procedure

A stirred suspension of 2-bromo-3-hydroxy-4-methoxybenzaldehyde (commercially available, 24 g, 104 mmol) and K2CO3 (29.4 g, 213 mmol) in DMF (125 ml) was cooled to −10° C. Dimethylsulfate (9.6 ml, 102 mmol) was added, the reaction was warmed to room temperature and stirred overnight. The resulting solution was quenched with water (375 ml) and the resulting suspension stirred overnight. The resulting suspension was filtered and the solid dried in vacuo at 50° C. to give 23.1 g of the subtitle product (91%).

Workup

  1. temperaturethe reaction was warmed to room temperature
  2. customThe resulting solution was quenched with water (375 ml)
  3. stirringthe resulting suspension stirred overnight
  4. filtrationThe resulting suspension was filtered
  5. customthe solid dried in vacuo at 50° C.

Sources & evidence

ORD record
ord-77781cbf596048309d1391566e70b02b
Source dataset
uspto-grants-2004_05
Patent number
US06734303B2

Reaction notes

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