Sulfuric Acid → Methyl 5-acetyl-2-(2-fluorophenylamino)-3,4-difluorobenzoate

HRID 558197노트

반응식

HRID 558197 반응식
[F:1][C:2]1[C:3]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])=[C:4]([CH:9]=[C:10]([C:13]#[C:14][Si](C)(C)C)[C:11]=1[F:12])[C:5]([O:7][CH3:8])=[O:6].[OH:27]S(O)(=O)=O>CC(C)=O>[C:13]([C:10]1[C:11]([F:12])=[C:2]([F:1])[C:3]([NH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:27])[CH3:14]

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 59519400Methyl 2-(2-fluorophenylamino)-3,4-difluoro-5-((trimethylsilyl)ethynyl)benzoate

생성물 1

HCID 59519431Methyl 5-acetyl-2-(2-fluorophenylamino)-3,4-difluorobenzoate수율 81%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a suspension of methyl 3,4-difluoro-2-(2-fluorophenylamino)-5-((trimethylsilyl)ethynyl)benzoate (1.20 g, 3.18 mmol) in 85% aqueous acetone (40 ml) were added HgSO4 (943 mg, 3.18 mmol) and H2SO4 (0.33 ml, 6.36 mmol). The reaction was heated at reflux for 24 h. The mixture was cooled to room temperature, concentrated, and diluted with EtOAc (100 ml). The organic solution was washed with H2O (50 ml), dried over Na2SO4 and concentrated. Silica gel chromatography (EtOAc:Hexanes=10:90) yielded 832 mg (81%) of methyl 5-acetyl-3,4-difluoro-2-(2-fluorophenylamino)benzoate as a white solid.

후처리

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 24 h
  3. concentrationconcentrated
  4. additiondiluted with EtOAc (100 ml)
  5. washThe organic solution was washed with H2O (50 ml)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8b7d177dd8fd42e18e42fe5bd4406f22
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063049B2

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