Imidazole → (2-(3-Bromophenyl)-2-fluoroethoxy)(tert-butyl)dimethylsilane

HRID 1689288Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1689288
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([F:11])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.N1C=CN=C1.[C:17]([Si:21]([CH3:24])([CH3:23])Cl)([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]([F:11])[CH2:9][O:10][Si:21]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:24])[CH3:23])[CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 579893062-(3-Bromophenyl)-2-fluoroethanol

Produkt 1

HCID 57989324(2-(3-Bromophenyl)-2-fluoroethoxy)(tert-butyl)dimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2-(3-bromophenyl)-2-fluoroethanol (example 39, step b) (1.38 g) and imidazole (1.29 g) in DMF (14 mL) was cooled in ice-water, treated with tert-butyldimethylchlorosilane (1.049 g), then removed from the cooling bath and stirred at room temperature overnight. The solution was poured into water and extracted twice with diethyl ether. The combined organic extracts were washed twice with water, once with brine, then dried over anhydrous magnesium sulphate and purified by flash chromatography on silica eluted with 10% dichloromethane in isohexane to afford the subtitled compound as a colourless oil. Yield 1.94 g.

Aufarbeitung

  1. customremoved from the cooling bath
  2. additionThe solution was poured into water
  3. extractionextracted twice with diethyl ether
  4. washThe combined organic extracts were washed twice with water, once with brine
  5. dry with materialdried over anhydrous magnesium sulphate
  6. custompurified by flash chromatography on silica
  7. washeluted with 10% dichloromethane in isohexane

Quellen und Nachweise

ORD-Eintrag
ord-beabb2395ff944f4813483442c923d73
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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