Dimethyl Sulfate → 5-Bromo-3-cyclobutyl-2-methoxybenzaldehyde

HRID 385048Notes

Reaction equation

HRID 385048 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]2[CH2:14][CH2:13][CH2:12]2)[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:15](=O)([O-])[O-].[K+].[K+].COS(=O)(=O)OC>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:11]2[CH2:12][CH2:13][CH2:14]2)[C:5]([O:10][CH3:15])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 866681565-Bromo-3-cyclobutyl-2-hydroxybenzaldehyde

Product 1

HCID 866681575-Bromo-3-cyclobutyl-2-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-bromo-3-cyclobutyl-2-hydroxybenzaldehyde was dissolved in N,N-dimethylformamide (30 mL), and potassium carbonate (10.79 g) and dimethylsulfuric acid (3.7 mL) were added to the solution under water cooling, and then the mixture was stirred at room temperature for 14 hours. The reaction solution was filtered and water was added, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1) to obtain the title compound (1.27 g) as a yellow oily substance.

Workup

  1. filtrationThe reaction solution was filtered
  2. additionwater was added
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-caf19eecd7774e679e70d6ddfa5d7e6a
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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