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

HRID 558197ノート

反応式

HRID 558197 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8b7d177dd8fd42e18e42fe5bd4406f22
出典データセット
uspto-grants-2011_11
特許番号
US08063049B2

反応ノート

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