Benzeneacetonitrile, 2-fluoro- → 2-(2-Fluorophenyl)-3-phenylpropanenitrile

Temperature

-78 °C

A solution of 2-(2-fluorophenyl)acetonitrile (2.1 g, 15.5 mol) in tetrahydrofuran (50 ml) and hexane (20 ml) was treated with n-butyl lithium (6.2 ml, 15.5 mol) at −78° C. The mixture was stirred at −78° C. for one hour. A solution of benzyl magnesium bromide (2.02 ml, 17.05 mmol) in hexane (10 ml) was added at −78° C. The mixture was stirred at −78° C. for two hours, then warmed to room temperature and stirred at room temperature overnight. The mixture was quenched with water and extracted in ether. The combined organic layers were washed with brine, dried with magnesium sulfate then filtered and evaporated. Purification by MPLC with 3 to 5% MeOH:CH2Cl2 afforded 2-(2-fluorophenyl)-3-phenylpropanenitrile, (Intermediate 11), (3.4 g).

1. stirringThe mixture was stirred at −78° C. for two hours
2. temperaturewarmed to room temperature
3. stirringstirred at room temperature overnight
4. customThe mixture was quenched with water
5. extractionextracted in ether
6. washThe combined organic layers were washed with brine
7. dry with materialdried with magnesium sulfate
8. filtrationthen filtered
9. customevaporated
10. customPurification by MPLC with 3 to 5% MeOH

ORD record

ord-178d9edb0e05455791ce5e9a85015316

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08735438B2