tert-Butylsulfonamide → N-(1-(5-bromo-2-fluorophenyl)-3-(tert-butyldimethylsilyloxy)-2,2-difluoropropylidene)-2-methylpropane-2-sulfinamide

HRID 81604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 81604
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:22])=[C:6]([C:8](=O)[C:9]([F:20])([F:19])[CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:7]=1.[CH3:23][C:24]([S:27]([NH2:30])(=O)=[O:28])([CH3:26])[CH3:25]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:22])=[C:6]([C:8](=[N:30][S:27]([C:24]([CH3:26])([CH3:25])[CH3:23])=[O:28])[C:9]([F:20])([F:19])[CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH:7]=1

Komponenten

4

Edukt 2

HCID 2757335tert-ButylsulfonamideHCID 666657711-(5-Bromo-2-fluorophenyl)-3-(tert-butyldimethylsilyloxy)-2,2-difluoropropan-1-one

Produkt 1

HCID 86650272N-(1-(5-bromo-2-fluorophenyl)-3-(tert-butyldimethylsilyloxy)-2,2-difluoropropylidene)-2-methylpropane-2-sulfinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1-(5-bromo-2-fluorophenyl)-3-(tert-butyldimethylsilyloxy)-2,2-difluoropropan-1-one (16.0 g, 40.4 mmol) in dry THF (350 mL) was added Ti(OEt)4 (16.7 mL, 80.4 mmol) and 2-Methyl-2-propane sulfonamide (5.8 g, 48.4 mmol) and refluxed for 16 h. Reaction mixture was concentrated under reduced pressure and the crude residue was directly purified by column chromatography on silica gel with 3% ethyl acetate in Hexane to furnish title compound as a colorless liquid. Yield=13.1 g (65.5%). TLC (10% ethyl acetate in Hexane): Rf=0.2),

Aufarbeitung

  1. temperaturerefluxed for 16 h
  2. customReaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. customthe crude residue was directly purified by column chromatography on silica gel with 3% ethyl acetate in Hexane

Quellen und Nachweise

ORD-Eintrag
ord-a5c164f675b84171bf5069ed12daae18
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846658B2

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