Reaktion #626656

Reaktionsgleichung

Sodium carbonate

2-chloroquinoline

(3-chlorophenyl)boronic acid

1,2-dimethoxyethane

→

2-(3-chlorophenyl)quinoline

Ausbeute 77.5%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas charged into the reaction flask
2. 2
   SonstigeThe reaction flask was then evacuated
3. 3
   workup.ADDITIONback-filled with nitrogen
4. 4
   Temperaturthen was heated
5. 5
   Temperaturto reflux for 20 hours
6. 6
   SonstigeThe organic layer was separated
7. 7
   Trocknendried over magnesium sulfate
8. 8
   FiltrationThe organics were filtered

Vorschrift

2-chloroquinoline (9.25 g, 56.5 mmol), (3-chlorophenyl)boronic acid (9.28 g, 59.4 mmol), Pd(PPh3)4 (1.634 g, 1.413 mmol) were charged into the reaction flask with 300 mL of 1,2-dimethoxyethane. Sodium carbonate (14.98 g, 141 mmol) was dissolved in 50 mL of water and was charged into the reaction flask. The reaction flask was then evacuated and back-filled with nitrogen then was heated to reflux for 20 hours. The organic layer was separated and dried over magnesium sulfate. The organics were filtered and stripped under vacuum. The crude residue was passed through a silica gel column using 5-25% ethyl acetate/hexanes yielding 2-(3-chlorophenyl)quinoline (10.5 g, 77% yield) as a white solid.

Quelle