N-(1-(5-bromo-2-fluorophenyl)-3-(tert-butyldimethylsilyloxy)-2,2-difluoropropylidene)-2-methylpropane-2-sulfinamide → N-(2-(5-bromo-2-fluorophenyl)-4-(tert-butyldimethylsilyloxy)-3,3-difluorobutan-2-yl)-2-methylpropane-2-sulfinamide

HRID 2196329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2196329
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:28])=[C:6]([C:8](=[N:21][S:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])[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.[CH3:29][Mg+].[Br-]>C(OCC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:28])=[C:6]([C:8]([NH:21][S:22]([C:24]([CH3:27])([CH3:26])[CH3:25])=[O:23])([C:9]([F:20])([F:19])[CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:16])[CH3:17])([CH3:14])[CH3:13])[CH3:29])[CH:7]=1

Komponenten

4

Edukt 2

HCID 86650272N-(1-(5-bromo-2-fluorophenyl)-3-(tert-butyldimethylsilyloxy)-2,2-difluoropropylidene)-2-methylpropane-2-sulfinamideHCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 66666208N-(2-(5-bromo-2-fluorophenyl)-4-(tert-butyldimethylsilyloxy)-3,3-difluorobutan-2-yl)-2-methylpropane-2-sulfinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
-35 °C

Versuchsvorschrift

To a solution of N-(1-(5-bromo-2-fluorophenyl)-3-(tert-butyldimethylsilyloxy)-2,2-difluoro-propylidene)-2-methylpropane-2-sulfinamide (12 g, 24.04 mmol) in diethyl ether (120 mL) was added CH3MgBr (3M in Diethyl ether) (41 mL, 120 mmol) at −25° C. The reaction mixture was brought to 0° C. and maintained for 30 min. Reaction mixture was again cooled to −35° C. and quenched by drop wise addition of saturated ammonium chloride solution. Organic layer was separated and washed with brine and dried over anhydrous sodium sulphate. Crude compound was purified by column chromatography on silica gel with 8% ethyl acetate in Hexane to furnish title compound as a colorless liquid. Yield=8.8 g (71%). TLC (20% ethyl acetate in Hexane): Rf=0.33),

Aufarbeitung

  1. customwas brought to 0° C.
  2. temperaturemaintained for 30 min
  3. customReaction mixture
  4. customquenched by drop wise addition of saturated ammonium chloride solution
  5. customOrganic layer was separated
  6. washwashed with brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customCrude compound was purified by column chromatography on silica gel with 8% ethyl acetate in Hexane

Quellen und Nachweise

ORD-Eintrag
ord-6c86f6a7e9b8477fa50caa28c540a17f
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338413B1

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