Reaktion #1133

Reaktionsgleichung

water

4-Bromophenol

imidazole

tert-butyldimethylsilyl chloride

→

title compound

4-Bromophenyl-tert-butyldimethylsilyl Ether

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate (2×75 mL)
2. 2
   WaschenThe combined extracts were washed with water (2×75 mL), brine (75 mL)
3. 3
   Trocknendried (MgSO4)
4. 4
   Einengenbefore concentration in vacuo
5. 5
   SonstigeThe crude product was purified

Vorschrift

4-Bromophenol (5.76 g, 30 mmol), imidazole (4.08 g, 60 mmol) and tert-butyldimethylsilyl chloride (5.02 g, 33 mmol) were stirred in anhydrous DMF (100 mL) at 25° C. for 18 h. The reaction mixture was then poured into water (100 mL) and extracted with ethyl acetate (2×75 mL). The combined extracts were washed with water (2×75 mL), brine (75 mL) and dried (MgSO4) before concentration in vacuo. The crude product was purified using "flash" silica gel column chromatography with ethyl acetate:hexane (1:4) as eluant to afford the title compound as an oil, 7.9 g, 92%. 1H NMR (CDCl3, 300 MHz): δ 7.33 (app. dt, J=9, 3, 1 Hz, 2 H), 6.73 (app. dt, J=9, 3, 1 Hz, 2 H) 0.98 (s, 9 H),0.21 (s, 6 H).

Quelle