Reaktion #5690

Reaktionsgleichung

indole

bromobenzene

potassium carbonate

DMF

→

1-phenylindole

Ausbeute 20.2%

Lösungsmittel

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated
2. 2
   Temperaturunder reflux for 43 hours
3. 3
   Extraktionextracted with 150 mL of ether
4. 4
   WaschenThe extract was washed with H2O (2×50 mL) and 50 mL of brine
5. 5
   Trocknendried over MgSO4
6. 6
   SonstigeThe oil was chromatographed on the solvent
7. 7
   workup.WAITleft 35.7 g of brown oil
8. 8
   SonstigeThe oil was chromatographed on a 1100 g column of silica gel
9. 9
   WaschenThe column was eluted with 25% CH2Cl2 -Skellysolve B and 200 mL fractions
10. 10
    Sonstigewere collected

Vorschrift

A mixture of 17.57 g (0.15 mole) of indole, 23.55 g (0.15 mole) of bromobenzene, 21 g of anhydrous potassium carbonate, 0.75 g of CuO, and 30 mL of DMF was stirred and heated under reflux for 43 hours. The cooled mixture was diluted with 200 mL of H2O and extracted with 150 mL of ether. The extract was washed with H2O (2×50 mL) and 50 mL of brine and dried over MgSO4. The oil was chromatographed on the solvent left 35.7 g of brown oil. The oil was chromatographed on a 1100 g column of silica gel. The column was eluted with 25% CH2Cl2 -Skellysolve B and 200 mL fractions were collected. The fractions were assayed by silica gel tlc (1×4") (25% CH2Cl2 -Skellysolve B). Fractions 15-22 were combined giving 5.86 g (20%) of 1-phenylindole as a yellow oil.

Quelle