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

HRID 558245ノート

反応式

HRID 558245 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[C:18]([F:19])=[C:17]([F:20])[C:16]([C:21]#[C:22][Si](C)(C)C)=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12].[OH:27]S(O)(=O)=O.O>CC(C)=O>[C:21]([C:16]1[C:17]([F:20])=[C:18]([F:19])[C:9]([NH:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])=[C:10]([CH:15]=1)[C:11]([O:13][CH3:14])=[O:12])(=[O:27])[CH3:22]

参加物

5

反応物 3

HCID 962WaterHCID 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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A mixture of methyl 2-(2-fluorophenylamino)-3,4-difluoro-5-((trimethylsilyl)ethynyl)benzoate (9 mmol, 3.5 g), HgSO4 (9 mmol, 2.67 g), and cone. H2SO4 (18 mmol, 0.96 ml) in acetone:H2O (70:12 ml) was refluxed at 65° C. overnight. The mixture was concentrated, diluted with EtOAc, and washed with water and brine. The organic fractions are combined, dried over MgSO4 and concentrated under reduced pressure. The crude material (brown solid) was triturated with MeOH and the precipitate was filtered, washed with additional MeOH and dried to yield the desired product in 60% (1.78 g).

後処理

  1. concentrationThe mixture was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material (brown solid) was triturated with MeOH
  7. filtrationthe precipitate was filtered
  8. washwashed with additional MeOH
  9. customdried

出典と根拠

ORDレコード
ord-86a4ca13797f4ac9902184a06f95ec4c
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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