Reaktion #1980176

Reaktionsgleichung

dichloromethane

1-pyreneboronic acid

6-Bromo-2-methylquinoline

Sodium hydrogencarbonate

→

required product

6-Pyrenyl-2-methylquinoline

Lösungsmittel

2-ethoxyethanol

2-ethoxy ethanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGwas stirred
2. 2
   Temperaturheated under nitrogen atmosphere at 90° C. for 18 h
3. 3
   Temperaturto cool
4. 4
   Filtrationthe reaction mixture was filtered through a layer of silica gel
5. 5
   workup.ADDITIONTo the filtrate further dichloromethane (50 ml) was added
6. 6
   Extraktionextracted with de-ionised water (2×100 ml)
7. 7
   TrocknenThe organic phase was dried over anhydrous magnesium sulphate
8. 8
   Sonstigethe solvent removed

Vorschrift

6-Bromo-2-methylquinoline (4.5; 20 mmole) was dissolved in 2-ethoxy ethanol (30 ml) and to the magnetically stirred solution under nitrogen was added tetrakis(triphenyl phosphine) palladium (1 g; 0.9 mmole). After 5 minutes stirring at room temperature, 1-pyreneboronic acid (5.0 g; 20 mmole) was added followed by 2-ethoxyethanol (10 ml). Sodium hydrogencarbonate (10 g; 94 mmole) in water (60 ml) was added all at once and the reaction mixture was stirred and heated under nitrogen atmosphere at 90° C. for 18 h. The reaction mixture was allowed to cool, dichloromethane (100 ml) was added and the reaction mixture was filtered through a layer of silica gel. To the filtrate further dichloromethane (50 ml) was added and extracted with de-ionised water (2×100 ml). The organic phase was dried over anhydrous magnesium sulphate and the solvent removed to give the required product. The product was dried under vacuum at 80° C., Yield 4.5 g (67%). Mp 133° C. (DSC, onset). Elemental analysis: Found C, 90.80; H, 5.09; N, 4.32; C26H17N requires C, 90.93; H, 4.99; and N, 4.08%.

Quelle