2-(4-fluorophenyl)cyclohexanol synthesis
- Product Name:2-(4-fluorophenyl)cyclohexanol
- CAS Number:851337-37-6
- Molecular formula:C12H15FO
- Molecular Weight:194.25
Yield:851337-37-6 56%
Reaction Conditions:
Stage #1: 1-Bromo-4-fluorobenzenewith n-butyllithium in diethyl ether at -78; for 0.0833333 h;
Stage #2: cyclohexane-1,2-epoxidewith boron trifluoride diethyl etherate in diethyl ether at -78 - -50; for 4 h;
Stage #3: with ammonium chloride in diethyl ether;water;
Steps:
a
a) 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 nL, 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).
References:
US2005/154001,2005,A1 Location in patent:Page/Page column 8
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