Water → 5-Bromo-3-isopropyl-2-methoxybenzaldehyde

HRID 385038Notes

Reaction equation

HRID 385038 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:11]([CH3:13])[CH3:12])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:14](=O)([O-])[O-].[K+].[K+].COS(=O)(=O)OC.O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([CH:11]([CH3:13])[CH3:12])[C:5]([O:10][CH3:14])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 592683215-Bromo-2-hydroxy-3-isopropylbenzaldehyde

Product 1

HCID 840479705-Bromo-3-isopropyl-2-methoxybenzaldehydeYield 97.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-bromo-2-hydroxy-3-isopropylbenzaldehyde (25.88 g) was dissolved in N,N-dimethylformamide (100 mL), and potassium carbonate (27.64 g) and dimethylsulfuric acid (9.5 mL) were added to the solution under water cooling, and the mixture was stirred at room temperature for 2 hours. Water was added to the reaction solution, and then the reaction mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (26.76 g) as a brown oily substance.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-461a6f8eb53249a094013100f2e9dd72
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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