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

HRID 494687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494687
[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>[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 865967735-Acetyl-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl esterAusbeute 73,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 2-(2-chlorophenylamino)-3,4-difluoro-5-trimethylsilanylethynylbenzoic acid methyl ester (5) (79.4 mg, 0.20 mmol), HgSO4 (59.8 mg, 2.0 mmol), and conc. H2SO4 (0.02 mL, 0.40 mmol) in 80% aqueous acetone (2.5 mL), were refluxed for 48 hours. The reaction was concentrated under reduced pressure, and diluted with EtOAc. The organic layer was washed with water and brine, dried over MgSO4 and concentrated to give 50.1 mg (73%) of the desired product (6).

Aufarbeitung

  1. temperaturewere refluxed for 48 hours
  2. concentrationThe reaction was concentrated under reduced pressure
  3. additiondiluted with EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c237c32ad39d4431a177d5647e051985
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538120B2

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