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

HRID 510867Notes

Reaction equation

HRID 510867 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 g, 38 mmol), dimethyl sulfate (4.3 mL, 46 mmol) and potassium carbonate (11 g, 76 mmol) in acetone (200 mL) was heated at reflux overnight. After evaporation to dryness, the mixture was diluted with water and extracted with ethyl acetate. 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% ethyl acetate in hexane, to yield the desired product (8.8 g, 84%). LCMS calculated for C10H11BrClO2 (M+H)+: m/z=277.0. 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 ethyl acetate
  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% ethyl acetate in hexane

Sources & evidence

ORD record
ord-df218c1ba3ac4043bdec1a2d2ff8a13f
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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