Dimethyl Sulfate → Methyl 4-bromo-3,5-dimethoxybenzoate

HRID 1454115노트

반응식

HRID 1454115 반응식
[Br:1][C:2]1[C:10](O)=[CH:9]C(C(O)=O)=[CH:4][C:3]=1[OH:12].[C:13](=O)([O-])[O-].[K+].[K+].S([O:24][CH3:25])(OC)(=O)=O.[C:26]([O:29][CH2:30]C)(=[O:28])[CH3:27]>>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[CH:4][C:27]([C:26]([O:29][CH3:30])=[O:28])=[CH:9][C:10]=1[O:24][CH3:25]

참가 물질

5

반응물 4

HCID 6497Dimethyl SulfateHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 860234-Bromo-3,5-dihydroxybenzoic acid

생성물 1

HCID 117713Methyl 4-bromo-3,5-dimethoxybenzoate

반응 조건

온도
65 °C

실험 절차

To a suspension of 4-bromo-3,5-dihydroxybenzoic acid (95.0 kg) in ethyl acetate (950 L) were added anhydrous potassium carbonate (270.8 kg) and dimethyl sulfate (174.7 kg). The mixture was heated at 50-80° C. for about 4 hours and partitioned by adding water. The organic layer was washed with water and saturated aqueous NaCl solution and concentrated under reduced pressure. The residue was suspended into methanol, stirred under heating and cooled. The crystalline precipitates were collected by filtration and dried to yield methyl 4-bromo-3,5-dimethoxybenzoate (98.8 kg) as pale yellow crystals.

후처리

  1. custompartitioned
  2. additionby adding water
  3. washThe organic layer was washed with water and saturated aqueous NaCl solution
  4. concentrationconcentrated under reduced pressure
  5. temperatureunder heating
  6. temperaturecooled
  7. customThe crystalline precipitates
  8. filtrationwere collected by filtration
  9. customdried

출처 및 근거

ORD 기록
ord-6f717bfc8cc1491dbf06b23c14eaf4a6
출처 데이터셋
uspto-grants-2009_01
특허 번호
US07476758B2

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