Reaktion #7909

Reaktionsgleichung

(4-chlorophenyl)acetonitrile

1,3-dibromopropane

dimethylsulfoxide

sodium hydride

→

1-(4-chlorophenyl)-cyclobutanecarbonitrile

Ausbeute 68.2%

Lösungsmittel

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a round-bottom flask under argon fitted with an addition funnel
2. 2
   Temperaturwhile maintaining the reaction temperature at 20–30° C
3. 3
   SonstigeThe reaction mixture was carefully quenched with water (50 mL)
4. 4
   Extraktionextracted with hexane (3×100 mL)
5. 5
   Waschenwashed with water (3×75 mL), brine (50 mL)
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Einengenconcentrated

Vorschrift

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.

Quelle