Reaktion #1668636

Reaktionsgleichung

4-cyanophenylboric acid

Na2CO3

quinoline

4-bromo-2,6-dimethylquinoline

→

4-(4-cyanophenyl)-2,6-dimethylquinoline

Ausbeute 88.2%

Lösungsmittel

methanol

water

toluene

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere mixed
2. 2
   Sonstigeto react for 22 hours in a nitrogen atmosphere at a temperature of 80° C
3. 3
   Extraktionextracted
4. 4
   TrocknenThe chloroform layer was dried
5. 5
   Sonstigethe Na2SO4 was removed
6. 6
   Filtrationby filtering
7. 7
   SonstigeThe solvent was removed under reduced pressure
8. 8
   Sonstigethe residue was purified through column chromatography (silica gel, hexane/ethyl acetate=2/1)

Vorschrift

In example 1-6, a compound represented by the chemical formula (38) was synthesized through the following processes as an example quinoline derivative. First, a solution in which 4-bromo-2,6-dimethylquinoline (1.05 g) identical to that in the example 1-4 and Pd(Ph3P)4 (0.31 g) were added to toluene (8.5 ml), a solution in which Na2CO3 (1.81 g) was added to water (8.5 ml), and a solution in which 4-cyanophenylboric acid (0.726 g) was added to methanol (2.8 ml) were mixed and allowed to react for 22 hours in a nitrogen atmosphere at a temperature of 80° C. The reaction solution was poured into water and extracted using chloroform. The chloroform layer was dried using Na2SO4 and the Na2SO4 was removed by filtering. The solvent was removed under reduced pressure and the residue was purified through column chromatography (silica gel, hexane/ethyl acetate=2/1) to obtain 4-(4-cyanophenyl)-2,6-dimethylquinoline (1.013 g) represented by the following chemical formula (48).

Quelle