Imidazole → [(3-Bromo-5-fluorobenzyl)oxy](tert-butyl)diphenylsilane

HRID 501897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 501897
N1C=CN=C1.[C:6]([Si:10]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)Cl)([CH3:9])([CH3:8])[CH3:7].[Br:24][C:25]1[CH:26]=[C:27]([CH2:32][OH:33])[CH:28]=[C:29]([F:31])[CH:30]=1.O>CN(C)C=O>[Br:24][C:25]1[CH:26]=[C:27]([CH:28]=[C:29]([F:31])[CH:30]=1)[CH2:32][O:33][Si:10]([C:6]([CH3:9])([CH3:8])[CH3:7])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 4

HCID 795ImidazoleHCID 962WaterHCID 94078tert-ButyldiphenylchlorosilaneHCID 2769402(3-Bromo-5-fluorophenyl)methanol

Produkt 1

HCID 58843476[(3-Bromo-5-fluorobenzyl)oxy](tert-butyl)diphenylsilaneAusbeute 87,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Imidazole (3.3 g) and tert-butyl-diphenylchlorosilane (10.0 g) were added to a solution of (3-bromo-5-fluorophenyl)methanol (5.0 g) in dimethylformamide (50 ml), and the mixture was stirred over night at room temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated saline solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated from the filtrate under reduced pressure to give the residue. The resulting residue was purified by silica gel column chromatography (n-hexane-ethyl acetate) to obtain [(3-bromo-5-fluorobenzyl)oxy](tert-butyl)diphenylsilane (9.5 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated saline solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter filtration
  5. customthe solvent was evaporated from the filtrate under reduced pressure
  6. customto give the residue
  7. customThe resulting residue was purified by silica gel column chromatography (n-hexane-ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-a11a1882d484466bae6ff2ff28a74ee2
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07772407B2

Notizen zur Reaktion

Wird geladen…