Isobutyronitrile → 5-chloro-2,2-dimethylpentanenitrile

Participants

Reaction Steps

To a solution of isobutyronitrile (13.8 g, 0.2 mol; Aldrich) in hexanes (200 mL) was added a 2M solution of lithium diisopropylamide (100 mL, 0.2 mol; Aldrich), and the mixture stirred for 2 hrs under nitrogen. This mixture was added to a solution of 1-bromo-3-chloropropane (34.6 g, 0.22 mol; Aldrich) and stirred for 1 h. The reaction was quenched by careful addition of water, and the hexane layer was dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (SiO2, 20–50% CH2Cl2 in Hexanes) to provide 10 g (68.7 mmol, Yield=34%) of the title compound as an amber oil: 1H NMR (CDCl3, 500 MHz) δ ppm: 1.35 (6H, s, gem-Me), 1.67 (2H, m, CH2), 1.95 (2H, m, CH2), 3.57 (2H, t, J=6.5 Hz, Cl-CH2); 13C NMR (CDCl3, 125.8 Hz) δ ppm 26.73, 28.50, 32.08, 38.47, 44.58, 124.72.

Provenance & Evidence