Cyclohexene oxide → 2-(4-Fluorophenyl)cyclohexan-1-one

Temperature

-50 °C

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).

1. customAfter 4 h at this temperature the reaction was quenched by the addition of ammonium chloride (saturated, 200 mL)
2. additiondiluted with water (50 mL)
3. extractionThe product was then extracted with diethylether (3×100 mL)
4. dry with materialthe combined organic extracts dried over sodium sulfate
5. filtrationFiltration and evaporation

ORD record

ord-a13c92e5d7244beda1f1ee616a217e11

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07173133B2