Reaktion #1963552

Reaktionsgleichung

potassium tert-butoxide

2-(2-bromo-4-chlorophenoxy)cyclopentanone

→

2-bromo-4-chloro-1-(2-methylenecyclopentyloxy)benzene

Ausbeute 58.2%

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added slowly
2. 2
   workup.STIRRINGThe resulting mixture was stirred at room temperature under nitrogen for 3 hours
3. 3
   SonstigeThe reaction mixture was quenched with water
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   WaschenThe organic phase was washed with water, brine
6. 6
   Trocknendried with sodium sulfate
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe residue was purified by flash chromatography on silica gel (5-10% EtOAc in hexanes)

Vorschrift

To the mixture of methyl triphenylphosphonium bromide (16.0 g, 44.8 mmol) in anhydrous tetrahydrofuran (125 mL) at 0° C. under nitrogen was added portion wise the potassium tert-butoxide (5.0 g, 44.8 mmol). After stirring at 0° C. for 30 minutes, the mixture of 2-(2-bromo-4-chlorophenoxy)cyclopentanone (516B) (10.8 g, 37.3 mmol) in tetrahydrofuran (40 mL) was added slowly. The resulting mixture was stirred at room temperature under nitrogen for 3 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic phase was washed with water, brine, dried with sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (5-10% EtOAc in hexanes) to provide 2-bromo-4-chloro-1-(2-methylenecyclopentyloxy)benzene (517) (6.2 g, 58.2%) as a colorless oil.

Quelle