Isobutyronitrile → 5-chloro-2,2-dimethylpentanenitrile

Participants

Reaction Steps

Isobutyronitrile (9.9 g, 0.143 mole) is added dropwise to a suspension of lithium dimethylamide (7.3 g, 0.143 mole) in hexanes. The resultant anion solution is added to a solution of 1-bromo-3-chloropropane (24.8 g, 0.16 mole) in hexane at 5° to 10° C., warmed to room temperature, and quenched with water. The phases are separated and the organic phase is concentrated in vacuo to afford the title product as a yellow oil, 19.0 g(80% pure, 90.9% yield), identified via gas chromatography.

Provenance & Evidence