Sulfuric Acid → 5-Acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester

HRID 500566노트

반응식

HRID 500566 반응식
[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([C:10]#[C:11][Si](C)(C)C)[C:7]([F:16])=[C:6]([F:17])[C:5]=1[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25].[OH:27]S(O)(=O)=O>CC(C)=O.O>[CH3:1][O:2][C:3](=[O:26])[C:4]1[CH:9]=[C:8]([C:10](=[O:27])[CH3:11])[C:7]([F:16])=[C:6]([F:17])[C:5]=1[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25]

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 865967722-(2-Chlorophenylamino)-3,4-difluoro-5-trimethylsilanylethynylbenzoic acid methyl ester

생성물 1

HCID 865967735-Acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester수율 73%

시약·촉매·용매 1

HCID 18366337Propan-2-one--water (1/1)용매

실험 절차

A mixture of 2-(2-chlorophenylamino)-3,4-difluoro-5-trimethylsilanylethynylbenzoic acid methyl ester (7.11 g, 18.1 mmol), HgSO4 (5.43 g, 18.1 mmol), and conc. H2SO4 (1.92 mL, 36.1 mmol) in acetone-water (150 mL/25 mL) was refluxed for 3 hours. The reaction mixture was concentrated in vacuo, diluted with EtOAc-THF, and washed with water and brine. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to give the crude material which was triturated with MeOH to afford the desired product (4.46 g, 73%).

후처리

  1. temperaturewas refluxed for 3 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with EtOAc-THF
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give the crude material which
  9. customwas triturated with MeOH

출처 및 근거

ORD 기록
ord-9d553e1f3bb74539a962ed6d2e6e8c0d
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772234B2

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