Dimethyl Sulfate → Ethyl 3-iodo-2,4-dimethoxy-6-methylbenzoate

HRID 2177847Notes

Reaction equation

HRID 2177847 reaction equation
O[C:2]1[C:12]([I:13])=[C:11]([OH:14])[CH:10]=[C:9]([CH3:15])[C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].COS([O:21][CH3:22])(=O)=O.[C:23](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[I:13][C:12]1[C:2]([O:21][CH3:22])=[C:3]([C:9]([CH3:15])=[CH:10][C:11]=1[O:14][CH3:23])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 10519838Ethyl 2,4-dihydroxy-3-iodo-6-methylbenzoate2×

Product 1

HCID 10915077Ethyl 3-iodo-2,4-dimethoxy-6-methylbenzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of ethyl 2,4-dihydroxy-3-iodo-6-methylbenzoate (Intermediate 204, 0.144 g), dimethylsulphate (0.085 ml) and potassium carbonate (0.185 g) in acetone (10 ml) was heated at reflux for 2.5 hours. After cooling, the mixture was filtered and the filtrate was evaporated to dryness. The residue was partitioned between DCM and water and the organic layer was filtered through a phase separator. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20% to give ethyl 3-iodo-2,4-dimethoxy-6-methylbenzoate (0.158 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2.5 hours
  3. temperatureAfter cooling
  4. filtrationthe mixture was filtered
  5. customthe filtrate was evaporated to dryness
  6. customThe residue was partitioned between DCM and water
  7. filtrationthe organic layer was filtered through a phase separator
  8. customThe filtrate was evaporated to dryness
  9. customthe residue was purified by chromatography on silica
  10. washeluting with a mixture of ethyl acetate and cyclohexane with a gradient of 0-20%

Sources & evidence

ORD record
ord-f6743098a12149aeab07f5b8dc351dcb
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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