Imidazole → tert-Butyl-(3,5-dibromobenzyloxy)diphenylsilane

HRID 2212319Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2212319
N1C=CN=C1.[Br:6][C:7]1[CH:8]=[C:9]([CH:12]=[C:13]([Br:15])[CH:14]=1)[CH2:10][OH:11].[Si:16](Cl)([C:29]([CH3:32])([CH3:31])[CH3:30])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C.C(OCC)(=O)C>[C:29]([Si:16]([O:11][CH2:10][C:9]1[CH:8]=[C:7]([Br:6])[CH:14]=[C:13]([Br:15])[CH:12]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([CH3:32])([CH3:30])[CH3:31]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 7009423(3,5-Dibromophenyl)methanol

Produkt 1

HCID 21964571tert-Butyl-(3,5-dibromobenzyloxy)diphenylsilaneAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

With stirring, imidazole (1.1 g, 16.0 mmol) is added to a solution of 3,5-dibromobenzyl alcohol (2.8 g, 10.5 mmol) in absolute DMF (20 ml), and the mixture is cooled to 0° C. tert-Butyldiphenylsilyl chloride (3.3 ml, 17.8 mmol) is added dropwise to the reaction solution, which is then stirred at 0° C. for 2 h. The mixture is then warmed to RT and stirred for another 2 h. The reaction mixture is diluted with ethyl acetate (20 ml) and extracted with a semisaturated aqueous NH4Cl solution (20 ml). The organic phase is dried over MgSO4, filtered off and concentrated under reduced pressure. Further purification is carried out by chromatography [PE/EA (99:1)] on a silica gel column. This gives the title compound (5.0 g) as a colorless solid. TLC, silica gel (glass plates), [petroleum ether/ethyl acetate (99:1)], Rf=0.8.

Aufarbeitung

  1. additionis added dropwise to the reaction solution, which
  2. stirringis then stirred at 0° C. for 2 h
  3. stirringstirred for another 2 h
  4. extractionextracted with a semisaturated aqueous NH4Cl solution (20 ml)
  5. dry with materialThe organic phase is dried over MgSO4
  6. filtrationfiltered off
  7. concentrationconcentrated under reduced pressure
  8. customFurther purification

Quellen und Nachweise

ORD-Eintrag
ord-b61e584ea3d64e6aaebcf1e04f10c912
Quelldatensatz
uspto-grants-2006_09
Patentnummer
US07101911B2

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