Hydrochloric Acid → HCID 58409088, compound

To a solution of 2-(2,4-dichlorophenyl)-2-fluoroacetonitrile (0.263 g, 1.29 mmol) in THF (2 ml) was added borane-DMS complex (0.134 ml, 1.42 mmol), and the reaction was heated to reflux under argon for one hour. The reaction was cooled to ambient temperature, and 0.4 ml of concentrated hydrochloric acid were added. The reaction mixture was again heated to reflux for 30 minutes, then cooled to ambient temperature and treated with 1M sodium hydroxide until the pH reached 13. The reaction was extracted three times with ether, and the combined organic layers were washed with saturated sodium chloride, dried over anhydrous potassium carbonate, filtered, and concentrated to yield 217 mg of the title compound (80.9% yield).

1. temperaturethe reaction was heated
2. temperatureto reflux under argon for one hour
3. temperatureThe reaction mixture was again heated
4. temperatureto reflux for 30 minutes
5. temperaturecooled to ambient temperature
6. extractionThe reaction was extracted three times with ether
7. washthe combined organic layers were washed with saturated sodium chloride
8. dry with materialdried over anhydrous potassium carbonate
9. filtrationfiltered
10. concentrationconcentrated

ORD record

ord-73bb612a948840b6a910f74d0b01ba6b

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08569522B2