Isobutyronitrile → 5-chloro-2,2-dimethylpentanenitrile

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.

1. stirringstirred for 1 h
2. customThe reaction was quenched by careful addition of water
3. dry with materialthe hexane layer was dried (Na2SO4)
4. filtrationfiltered
5. concentrationconcentrated
6. customThe residue was purified by column chromatography (SiO2, 20–50% CH2Cl2 in Hexanes)

ORD record

ord-bd4c44a864564ddab503e738b986f398

Source dataset

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07173022B2