Water → 5-Bromo-2-methoxy-3-(trifluoromethyl)benzaldehyde

HRID 385013Notes

Reaction equation

HRID 385013 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:13])[F:12])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:15](=O)([O-])[O-].[K+].[K+].COS(=O)(=O)OC.O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([F:12])([F:13])[F:14])[C:5]([O:10][CH3:15])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 27792785-Bromo-2-hydroxy-3-(trifluoromethyl)benzaldehyde

Product 1

HCID 840703065-Bromo-2-methoxy-3-(trifluoromethyl)benzaldehydeYield 98.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-bromo-2-hydroxy-3-trifluoromethylbenzaldehyde (63.98 g) was dissolved in N,N-dimethylformamide (130 mL), and potassium carbonate (65.79 g) and dimethylsulfuric acid (31.6 mL) were added to the solution under water cooling, and then the mixture was stirred at room temperature for 3 hours. Water was added to the reaction solution, and then the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound (66.19 g) as a brown crystal.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 1N hydrochloric acid 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-d155db9a08a245189aab07163777c986
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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