Cyclohexene oxide → 2-(4-Fluorophenyl)cyclohexanol

Temperature

-78 °C

To a cooled solution of 4-Fluorophenylmagnesium bromide (1.0M in THF, 4.94 mL, 4.94 mmol) in dry THF (10 mL) at −78° C. is added Copper (I) Bromide Dimethylsulfide complex (51 mg, 0.25 mmol) and the resulting mixture is stirred at −78° C. for 10 min, followed by the slow addition of a solution of 7-Oxa-bicyclo[4.1.0]heptane (500 μL, 4.94 mmol) in THF (2 mL). The reaction is warmed to 0° C. and is stirred for 2 hour. Then the reaction is quenched with saturated NH4Cl solution (20 mL). The resulting mixture is extracted with EtOAc (10 mL×3). The organic layers are combined, washed with brine (10 mL×1), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude is purified by silica flash column chromatography using EtOAc in Heptane (gradient from 0% to 35%) to give 700 mg of desired product.

1. temperatureThe reaction is warmed to 0° C.
2. stirringis stirred for 2 hour
3. customThen the reaction is quenched with saturated NH4Cl solution (20 mL)
4. extractionThe resulting mixture is extracted with EtOAc (10 mL×3)
5. washwashed with brine (10 mL×1)
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe crude is purified by silica flash column chromatography

ORD record

ord-b55a42d1ac0b4c0cbea41296ba13e4dd

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722709B2