1-Bromo-2-Chloroethane → HCID 86694105, compound

Temperature

50 °C

Sodium hydride (60% in oil, 0.620 g, 15.5 mmol) was washed with hexanes (2×10 mL) under nitrogen. Dry dimethylformamide (5 mL) was added and the suspension cooled in an acetone/ice bath. A solution of 2-(2-chloro-5-fluoropyridin-3-yl)acetonitrile (0.571 g, 3.35 mmol) in dry dimethylformamide (10 mL) was added slowly and the reaction stirred for minutes. 1-Bromo-2-chloroethane (0.300 ml, 3.60 mmol) was added. After stirring in the cold bath for 5 minutes, the orange mixture was removed from the cold bath and heated at 50° C. After 45 minutes the mixture was cooled and carefully quenched by addition of saturated ammonium chloride (10 mL) then partitioned between 10% saturated ammonium chloride (200 mL) and ethyl acetate (300 mL). The organic was dried with magnesium sulfate and evaporated to dryness under reduced pressure. The crude product was purified using silica chromatography (hexane to ethyl acetate gradient) to give the desired 1-(2-chloro-5-fluoropyridin-3-yl)cyclopropanecarbonitrile (0.400 g, 2.034 mmol, 60.8% yield).

1. temperaturethe suspension cooled in an acetone/ice bath
2. stirringAfter stirring in the cold bath for 5 minutes
3. customthe orange mixture was removed from the cold bath
4. temperatureAfter 45 minutes the mixture was cooled
5. customcarefully quenched by addition of saturated ammonium chloride (10 mL)
6. customthen partitioned between 10% saturated ammonium chloride (200 mL) and ethyl acetate (300 mL)
7. dry with materialThe organic was dried with magnesium sulfate
8. customevaporated to dryness under reduced pressure
9. customThe crude product was purified

ORD record

ord-8f53ec7573094e17a3a111dbc184844d

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09174992B2