Dimethyl Sulfate → 1-(5-Chloro-3-iodo-2-methoxy-4-methylphenyl)ethanone

HRID 510872Notes

Reaction equation

HRID 510872 reaction equation
[Cl:1][C:2]1[C:3]([CH3:13])=[C:4]([I:12])[C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.S(OC)(O[CH3:18])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[C:3]([CH3:13])=[C:4]([I:12])[C:5]([O:11][CH3:18])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 114723941-(5-Chloro-2-hydroxy-3-iodo-4-methylphenyl)ethanone

Product 1

HCID 866667971-(5-Chloro-3-iodo-2-methoxy-4-methylphenyl)ethanoneYield 86.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-(5-chloro-2-hydroxy-3-iodo-4-methylphenyl)ethanone (10 g, 32 mmol), dimethyl sulfate (3.7 mL, 39 mmol) and potassium carbonate (8.9 g, 64 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, filtered 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 (8.99 g, 86%). LCMS calculated for C10H11ClIO2 (M+H)+: m/z=324.9. found: 324.9.

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. filtrationfiltered
  9. customevaporated to dryness
  10. customThe residue was purified on silica gel
  11. washeluting with 0 to 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-116b77902ac04e9d98759461d86486a8
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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