Imidazole → [(4'-Bromobiphenyl-4-yl)methoxy](tert-butyl)dimethylsilane

HRID 1626779Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1626779
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.N1C=CN=C1.[C:21]([Si:25]([CH3:28])([CH3:27])Cl)([CH3:24])([CH3:23])[CH3:22].O>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][O:15][Si:25]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:28])[CH3:27])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 1393673[4-(4-Bromophenyl)phenyl]methanol

Produkt 1

HCID 68193270[(4'-Bromobiphenyl-4-yl)methoxy](tert-butyl)dimethylsilaneAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(4′-Bromobiphenyl-4-yl)methanol (0.70 g, 2.7 mmol) and imidazole (0.54 g, 8.0 mmol) were dissolved in tetrahydrofuran (20 mL), and tert-butyldimethylchlorosilane (1.2 g, 8.0 mmol) was added under a nitrogen atmosphere, followed by stirring at room temperature for 1 hour. Water was added to the reaction solution, which was extracted with ethyl acetate, and subsequently washed sequentially with a saturated sodium hydrogencarbonate solution, water and a saturated aqueous sodium chloride solution. After the organic layer was concentrated under reduced pressure, the resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate), and a fraction corresponding to the Rf value=0.90 (hexane/ethyl acetate=9/1) by thin layer chromatography was concentrated under reduced pressure to afford the title compound (0.92 g, 2.4 mmol) as a white solid (yield 91%).

Aufarbeitung

  1. extractionwas extracted with ethyl acetate
  2. washsubsequently washed sequentially with a saturated sodium hydrogencarbonate solution, water
  3. concentrationAfter the organic layer was concentrated under reduced pressure
  4. customthe resulting residue was purified by chromatography on a silica gel column (Moritex Corporation, elution solvent: hexane/ethyl acetate)
  5. concentrationa fraction corresponding to the Rf value=0.90 (hexane/ethyl acetate=9/1) by thin layer chromatography was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-e1239637e5de4dcda94efded4ccbb586
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785462B2

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