Cesium carbonate → 4-(4-Hydroxy-phenylsulfanyl)-3-nitro-benzoic acid methyl ester

HRID 605348노트

반응식

HRID 605348 반응식
[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7](Cl)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1.[SH:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[CH3:1][O:2][C:3](=[O:14])[C:4]1[CH:9]=[CH:8][C:7]([S:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[C:6]([N+:11]([O-:13])=[O:12])[CH:5]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 2401474-MercaptophenolHCID 735797Methyl 4-chloro-3-nitrobenzoate

생성물 1

HCID 668084784-(4-Hydroxy-phenylsulfanyl)-3-nitro-benzoic acid methyl ester

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of 4-chloro-3-nitrobenzoic acid methyl ester (4.00 g, 18 mmol) and 4-mercaptophenol (2.37 g, 18 mmol) in acetone (60 mL) was added Cs2CO3 (5.93 g, 18 mmol) at room temperature, and then the mixture was refluxed for 30 minutes. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated. The residue was diluted with AcOEt (30 mL), washed with H2O (3 times) and brine, dried over MgSO4, and evaporated to give brown oil. The oily residue was separated by silica gel column chromatography (n-hexane/AcOEt=4/3) to give the title compound as yellow amorphous (5.60 g).

후처리

  1. temperaturethe mixture was refluxed for 30 minutes
  2. filtrationthe mixture was filtered
  3. customthe filtrate was evaporated
  4. additionThe residue was diluted with AcOEt (30 mL)
  5. washwashed with H2O (3 times) and brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customto give brown oil
  9. customThe oily residue was separated by silica gel column chromatography (n-hexane/AcOEt=4/3)

출처 및 근거

ORD 기록
ord-73230ab517004cdf96b6709bae134bd6
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910595B2

반응 노트

불러오는 중…