Reaktion #325939

Reaktionsgleichung

3-bromo-5-fluorophenol

imidazole

tert-butyldiphenyl-silyl chloride

→

(3-bromo-5-fluorophenoxy)(tert-butyl)diphenylsilane

Ausbeute 58.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was quenched with water
2. 2
   Extraktionextracted with hexane/EtOAc (1:1)
3. 3
   WaschenThe combined organic layers were washed with H2O (2×) and sat. NaCl (2×)
4. 4
   Trocknendried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under reduced pressure
7. 7
   SonstigeThe resulting residue was purified by silica gel chromatography (hexanes/EtOAc)

Vorschrift

To a solution of 3-bromo-5-fluorophenol (5.7 g, 30 mmol), prepared as described in Procedure 3, and imidazole (4.0 g, 60 mmol, 2 eq) in anhydrous THF (100 mL) at 0° C. was added tert-butyldiphenyl-silyl chloride (9.6 mL, 1.3 eq). The resulting mixture was stirred at room temperature for 18 h. The reaction mixture was quenched with water and extracted with hexane/EtOAc (1:1). The combined organic layers were washed with H2O (2×) and sat. NaCl (2×), dried over Na2SO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexanes/EtOAc) to give (3-bromo-5-fluorophenoxy)(tert-butyl)diphenylsilane as colorless oil (7.5 g, yield 58%).

Quelle