Dimethyl Sulfate → Methyl 4-iodo-3-methoxybenzoate

HRID 70286

반응식

HRID 70286 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

HCID 11243290Methyl 4-iodo-3-methoxybenzoate

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3fc5470298f94a3ab2e31e37113df2e4
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822518B2

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