Water → {3-[(4-Bromophenyl)sulfanyl]propoxy}(tert-butyl)dimethylsilane

HRID 70581

Reaktionsgleichung

Reaktionsgleichung von HRID 70581
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].[Br:19][C:20]1[CH:25]=[CH:24][C:23]([SH:26])=[CH:22][CH:21]=1.O>CN(C)C=O>[Br:19][C:20]1[CH:25]=[CH:24][C:23]([S:26][CH2:8][CH2:9][CH2:10][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])=[CH:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilane

Produkt 1

HCID 58452783{3-[(4-Bromophenyl)sulfanyl]propoxy}(tert-butyl)dimethylsilaneAusbeute 95,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Potassium carbonate (4.1 g) and (3-bromopropoxy)-tert-butyldimethylsilane (4.1 g) were added to a solution of 4-bromothiophenol (3.0 g) in N,N-dimethylformamide, and the mixture was stirred at room temperature overnight. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1→20:1) to give the title compound as a colorless oil (5.5 g).

Aufarbeitung

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1→20:1)

Quellen und Nachweise

ORD-Eintrag
ord-89f6114bf4d848c3aab847590a690aff
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822503B2

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