Dimethyl Sulfoxide → 1-(4-Chlorophenyl)cyclobutanecarbonitrile

Temperatur

25 °C

Into a round-bottom flask under argon fitted with an addition funnel and thermometer was added anhydrous dimethylsulfoxide and sodium hydride (1.17 g, 48.8 mmol, 95%). Then a solution of (4-chlorophenyl)acetonitrile (A) (2.70 mL, 22.2 mmol) and 1,3-dibromopropane (2.48 mL, 24.4 mmol) in diethyl ether (15 mL) was added slowly, while maintaining the reaction temperature at 20-30° C. The reaction mixture was maintained at room temperature for overnight. The reaction mixture was carefully quenched with water (50 mL) and then extracted with hexane (3×100 mL). The organic extracts were combined, washed with water (3×75 mL), brine (50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated to give 2.9 g of 1-(4-chlorophenyl)-cyclobutanecarbonitrile, B, as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 2.03-2.09 (m, 1H); 2.36-2.62 (m, 3H); 2.76-2.84 (m, 2H); 7.34 (s, 4H); 13C NMR (CDCl3, 75 MHz): δ 17.0, 34.6 (2C), 39.7,123.9, 127.1, 129.1, 133.7, 138.3.

1. customInto a round-bottom flask under argon fitted with an addition funnel
2. temperatureThe reaction mixture was maintained at room temperature for overnight
3. customThe reaction mixture was carefully quenched with water (50 mL)
4. extractionextracted with hexane (3×100 mL)
5. washwashed with water (3×75 mL), brine (50 mL)
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated

ORD-Eintrag

ord-8c8e9e85eb6d4f0f92dfdda91199c0ff

Quelldatensatz

uspto-grants-2004_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06699866B2