Reaktion #1901481

Reaktionsgleichung

Potassium fluoride

allyl tributyl stannane

5-Bromo-quinoline

→

5-allyl-quinoline

Ausbeute 95.9%

Lösungsmittel

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was refluxed overnight
2. 2
   Temperaturcooled
3. 3
   Filtrationfiltered
4. 4
   EinengenThe reaction mixture was concentrated in vacuo
5. 5
   SonstigeIt was chromatographed in 3:1 hexane/ethyl acetate

Vorschrift

5-Bromo-quinoline (5.6 g, 27 mmol) was dissolved in 40 mL toluene. BHT (50 mg) was added, along with allyl tributyl stannane (9.3 mL, 30 mmol), and tetrakis(triphenyl)phospine palladium (600 mg, 0.52 mmol). The reaction was refluxed overnight, then cooled. Potassium fluoride solution (1.0 g, in 18 mL H2O) was added. The reaction was stirred for 3 hours, then filtered. The reaction mixture was concentrated in vacuo. It was chromatographed in 3:1 hexane/ethyl acetate to yield 4.38 g (95%) of 5-allyl-quinoline as a yellow oil. MS (APCI) m/z 170.1 (M+1).

Quelle