Reaktion #1980175

Reaktionsgleichung

Sodium hydrogencarbonate

dichloromethane

1-naphthaleneboronic acid

6-Bromo-2-methylquinoline

→

6-(1-Naphthyl)-2-methyl quinoline

Lösungsmittel

water

diethyl ether

2-ethoxyethanol

2-ethoxy ethanol

2-ethoxy ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   Temperaturto cool
3. 3
   Filtrationthe reaction mixture was filtered off under suction
4. 4
   workup.ADDITIONTo the filtrate further dichloromethane (250 ml) was added
5. 5
   Extraktionextracted with de-ionised water (2×300 ml) and finally with brine (250 ml)
6. 6
   TrocknenThe organic phase was dried over anhydrous magnesium sulphate
7. 7
   Sonstigethe solvent removed
8. 8
   Sonstigeto give a thick liquid
9. 9
   Sonstigegave a light yellow solid
10. 10
    SonstigeThe product was dried under vacuum at 80° C.

Vorschrift

6-Bromo-2-methylquinoline (32.5; 0.145 mole) was dissolved in 2-ethoxy ethanol (200 ml) and to the magnetically stirred solution under nitrogen was added tetrakis(triphenyl phosphine) palladium (5.1 g; 0.0044 mole) followed by 2-ethoxy ethanol (25 ml). After 5 minutes stirring at room temperature 1-naphthaleneboronic acid (25.0 g; 0.145 mole) was added followed by 2-ethoxyethanol (75 ml). Sodium hydrogencarbonate (35 g; 0.42 mole) in water (200 ml) was added all at once and the reaction mixture was stirred and heated under nitrogen atmosphere at 90° C. for 20 h. After 1 h, the reaction mixture became orange in colour. The reaction mixture was allowed to cool, dichloromethane (100 ml) was added and the reaction mixture was filtered off under suction using celite, with a layer of silica gel on the top. To the filtrate further dichloromethane (250 ml) was added, extracted with de-ionised water (2×300 ml) and finally with brine (250 ml). The organic phase was dried over anhydrous magnesium sulphate and the solvent removed to give a thick liquid. Trituration with diethyl ether and cooling in the refrigerator gave a light yellow solid. The product was dried under vacuum at 80° C., (22 g; 56%). Mp 111° C. (DSC, onset). Elemental analysis: Found C, 89.16; H, 5.58; N, 5.15; C20H15N requires C, 89.19; H, 5.61; and N, 5.20%.

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