Dimethyl Sulfate → Methyl 4-iodo-3-methoxybenzoate

HRID 70286

Reaktionsgleichung

Reaktionsgleichung von HRID 70286
O[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[I:11])[C:5]([OH:7])=[O:6].[C:12](=O)([O-])[O-].[K+].[K+].S([O:23][CH3:24])(OC)(=O)=O>CC(C)=O>[I:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([O:7][CH3:12])=[O:6])=[CH:3][C:2]=1[O:23][CH3:24]

Komponenten

5

Edukt 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 7368543-Hydroxy-4-iodobenzoic acid

Produkt 1

HCID 11243290Methyl 4-iodo-3-methoxybenzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

To a solution of 3-hydroxy-4-iodobenzoic acid (3.0 g, 0.011 mol) in acetone (50 mL) was added in one portion potassium carbonate (3.9 g, 0.028 mol). Dimethyl sulfate (3.5 g, 0.028 mol) was added dropwise and the mixture was heated at reflux overnight. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and aqueous saturated sodium bicarbonate solution. The organic phase was washed with brine, dried over sodium sulfated and concentrated in vacuo to give methyl 4-iodo-3-(methyloxy)benzoate as a yellow oil. 1H NMR (DMSO-d6) δ ppm 3.83 (s, 3H, Me), 3.87 (s, 3H, Me), 7.30 (dd, J=8.0, 1.8 Hz, 1H, Ar), 7.40 (d, J=1.7 Hz, 1H, Ar), 7.92 (d, J=8.0 Hz, 1H, Ar).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was partitioned between ethyl acetate and aqueous saturated sodium bicarbonate solution
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3fc5470298f94a3ab2e31e37113df2e4
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822518B2

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