Reaktion #965641

Reaktionsgleichung

sodium hydroxide

(5-bromo-3-chloro-pyridin-2-yl)-acetonitrile

1-bromo-2-chloroethane

hydrochloric acid

→

1-(5-bromo-3-chloro-pyridin-2-yl)-cyclopropanecarbonitrile

Ausbeute 81.8%

Lösungsmittel

diethyl ether

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturSubsequently, the reaction mixture was cooled to 0° C.
2. 2
   Sonstigeto obtain pH=1 (about 10 ml)
3. 3
   ExtraktionThe reaction mixture was extracted with two 50 ml portions of ethyl acetate
4. 4
   WaschenThe organic phase was washed with brine
5. 5
   Trocknendried over sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated
8. 8
   Sonstige1.16 g of crude material was obtained as a pale brown sticky solid
9. 9
   Filtrationthe orange suspension was filtered
10. 10
    EinengenThe filtrate was concentrated

Vorschrift

1.38 g of sodium hydroxide was dissolved in 40 ml of water and 0.93 g of benzyltriethylammonium chloride was added at ambient temperature. A solution of 1.00 g of (5-bromo-3-chloro-pyridin-2-yl)-acetonitrile (step 1) in 1.31 g of 1-bromo-2-chloroethane was then added dropwise. Then the reaction mixture was stirred at 60° C. for 2.5 hours. Subsequently, the reaction mixture was cooled to 0° C. and 36% aqueous hydrochloric acid was added in order to obtain pH=1 (about 10 ml). The reaction mixture was extracted with two 50 ml portions of ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated. 1.16 g of crude material was obtained as a pale brown sticky solid. The crude material was stirred in diethyl ether and the orange suspension was filtered. The filtrate was concentrated to give 910 mg of 1-(5-bromo-3-chloro-pyridin-2-yl)-cyclopropanecarbonitrile as an orange oil. 1H-NMR (CDCl3): 8.96 ppm (s, 1H), 7.92 ppm (s, 1H), 1.75 ppm (m, 2H), 1.60 ppm (m, 2H).

Quelle