Imidazole → [(6-Bromonaphthalen-2-yl)oxy](tert-butyl)dimethylsilane

HRID 259790

Reaktionsgleichung

Reaktionsgleichung von HRID 259790
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([OH:12])[CH:6]=[CH:5]2.N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].[SiH3]Cl>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:6]=[CH:5]2

Komponenten

6

Edukt 4

HCID 795Imidazole2×HCID 271446-Bromo-2-naphthalenolHCID 28928tert-Butyldimethylsilyl chlorideHCID 61622Chlorosilane

Produkt 1

HCID 13473083[(6-Bromonaphthalen-2-yl)oxy](tert-butyl)dimethylsilaneAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Bromo-2-naphthol (10 g, 44 mmol), imidazole (7.4 g, 110 mmol), and t-butyldimethylsilyl chloride (10 g, 66 mmol) were stirred in DMF (50 mL) at room temperature overnight. TLC analysis indicated incomplete reaction, so additional imidazole (0.6 g) and silyl chloride (1.3 g) were added, and stirring continued 1 day. After evaporation of DMF, the mixture was extracted with EtOAc and 5% aqueous KHSO4, dried (Na2SO4), and evaporated. The crude product was purified by silica gel chromatography, eluting with hexane, to yield a colorless solid (11 g). mp 62°-63° C. 1H NMR (300 MHz, CDCl3): 7.90 (d, 1H, J=l Hz), 7.62 (d, 1H, J=9 Hz), 7.55 (d, 1H, J=9 Hz), 7.46 (dd, 1H, J=9, 2 Hz), 7.14 (d, 1H, J=2 Hz), 7.08 (dd, 1H, J=9,2 Hz), 1.00 (s, 9H), 0.23 (s, 6H). MS(CH4): 365 (20%, M+C2H5, 1 Br isotope pattern), 337 (base, M+H, 1 Br isotope pattern).

Aufarbeitung

  1. customreaction
  2. customAfter evaporation of DMF
  3. extractionthe mixture was extracted with EtOAc and 5% aqueous KHSO4
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with hexane

Quellen und Nachweise

ORD-Eintrag
ord-a5d80d7583b246718f86a6891c700862
Quelldatensatz
uspto-grants-1996_06
Patentnummer
US05523302

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