반응 #434479

반응 방정식

cyclohexenoxide

1-bromo-4-fluorobenzene

BuLi

→

compound

수율 56.8%

rac-2-(4-Fluoro-phenyl)-cyclohexanone

수율 56.8%

용매

diethylether

반응 조건

후처리

1. 1
   기타After 4 h at this temperature the reaction was quenched by the addition of ammonium chloride (saturated, 200 mL)
2. 2
   workup.ADDITIONdiluted with water (50 mL)
3. 3
   추출The product was then extracted with diethylether (3×100 mL)
4. 4
   건조the combined organic extracts dried over sodium sulfate
5. 5
   여과Filtration and evaporation

실험 절차

To a solution of 1-bromo-4-fluorobenzene (12.5 mL, 114 mmol) in diethylether (250 mL) at −78° C. was added BuLi (1.6 M, 68 mL, 109 mmol) under argon. After 5 min at this temperature, cyclohexenoxide (11.0 mL, 109 mmol) was added followed by the addition of borontrifluoride-diethyletherate (13.8 mL, 109 mmol) whereby the temperature increased to approx. −50° C. After 4 h at this temperature the reaction was quenched by the addition of ammonium chloride (saturated, 200 mL) and diluted with water (50 mL). The product was then extracted with diethylether (3×100 mL) and the combined organic extracts dried over sodium sulfate. Filtration and evaporation afforded the tide compound (11.9 g, 56%) as white crystals after trituration from hexane. MS: m/e=194.1 (M).

출처