Dimethyl Sulfate → 1-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethanone

HRID 2274110Notes

Reaction equation

HRID 2274110 reaction equation
[Br:1][C:2]1[C:3]([OH:13])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].S(OC)(O[CH3:18])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Br:1][C:2]1[C:3]([O:13][CH3:18])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 120274791-(3-Bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone

Product 1

HCID 866667591-(3-Bromo-5-chloro-2-methoxy-4-methylphenyl)ethanoneYield 84%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-(3-bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone (10.0 g, 37.9 mmol), dimethyl sulfate (4.31 mL, 45.5 mmol) and potassium carbonate (10.5 g, 75.9 mmol) in acetone (200 mL) was heated at reflux overnight. After evaporation to dryness, the mixture was diluted with water, and extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, and evaporated to dryness. The residue was purified on silica gel, eluting with 0 to 20% EtOAc in hexane, to yield the desired product (8.8 g, 84%). LCMS calculated for C10H11BrClO2 (M+H)+: m/z=227.0. found: 277.0.

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. customAfter evaporation to dryness
  4. additionthe mixture was diluted with water
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated to dryness
  9. customThe residue was purified on silica gel
  10. washeluting with 0 to 20% EtOAc in hexane

Sources & evidence

ORD record
ord-32327ce0990540ac8263359f7693eced
Source dataset
uspto-grants-2015_09
Patent number
US09126948B2

Reaction notes

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