Acetonitrile → 3-(2,6-Dichlorophenyl)-3-oxopropiononitrile

Temperature

-78 °C

n-Butyl lithium (20.1 mL, 32.2 mmol, 1.6M in hexanes) was added to THF (30 mL) and the solution was cooled to −78° C. Acetonitrile (1.7 mL, 32 mmol) was added dropwise and the reaction stirred at the temperature for 45 minutes. Methyl 2,6-dichlorobenzoate (1.00 g, 4.88 mmol) was dissolved in 2 mL THF and added to the reaction mixture. The reaction stirred at −78° C. for 0.5 hr. The solution was quenched with methanol and warmed to room temperature. The material was diluted with water and 1N HCl. The solution was then extracted with Ethyl acetate, dried, and concentrated to give 1.08 g of desired product at 85% purity. Material used as is in the next step.

1. additionadded to the reaction mixture
2. stirringThe reaction stirred at −78° C. for 0.5 hr
3. customThe solution was quenched with methanol
4. temperaturewarmed to room temperature
5. additionThe material was diluted with water and 1N HCl
6. extractionThe solution was then extracted with Ethyl acetate
7. customdried
8. concentrationconcentrated

ORD record

ord-77175a3bf88e461f971e10ca09d4c908

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07897607B2