1,1-Dibromoethane → 1-(2,6-Dichloropyridin-3-yl)cyclopropane-1-carbonitrile

Participants

Reaction Conditions

Reaction Steps

5.92 g of sodium hydride (60% in oil) was suspended in 200 ml of dry THF and 10.13 g of (2,6-dichloro-pyridin-3-yl)-acetonitrile in 25 mL of dry THF was added dropwise at 0° C. The reaction mixture was stirred at 0° C. until the end of gas formation. Then 37.4 g of dibromoethane was added at 0° C. and the reaction mixture was stirred at ambient temperature for 14 h. Subsequently, the reaction mixture was quenched with 60 ml of aqueous saturated ammonium chloride. The reaction mixture was extracted with two 500 ml portions of ethyl acetate. The organic phase was washed with brine, dried over sodium sulphate, filtered and concentrated. 19 g of crude material was obtained as a dark solid which was purified by flash chromatography on silica gel with cyclohexane/ethyl acetate (4:1) as a solvent. Thus, 7 g of 1-(2,6-dichloro-pyridin-3-yl)-cyclopropanecarbonitrile was obtained as an orange solid. 1H-NMR (CDCl3): 7.64 ppm (d, 1H), 7.30 ppm (d, 1H), 1.83 ppm (m, 2H), 1.36 ppm (m, 2H).

Provenance & Evidence