Reaktion #1483121

Reaktionsgleichung

9-bromophenanthrene

2-formylphenylboronic acid

sodium carbonate

→

9-(2-formylphenyl)phenanthrene

Ausbeute 89.0%

Lösungsmittel

dimethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe resultant was refluxed
2. 2
   Temperaturwhile heating for 8 hours
3. 3
   Sonstigean aqueous phase was removed
4. 4
   SonstigeAn organic phase which had been separated
5. 5
   Waschenwas washed with water and saturated brine
6. 6
   Trocknendried with magnesium sulfate
7. 7
   FiltrationAfter the magnesium sulfate was filtered out
8. 8
   Einengenthe organic phase was concentrated
9. 9
   SonstigeThe resulting residue was purified by means of silica gel column chromatography

Vorschrift

Under an argon atmosphere, 25.7 g of 9-bromophenanthrene, 16.5 g of 2-formylphenylboronic acid and 2.31 g of tetraxis(triphenylphosphine)palladium(0) were placed in a flask. 340 mL of dimethyl ether (DME) and 170 mL of a 2M aqueous sodium carbonate solution were added to this flask, and the resultant was refluxed with stirring while heating for 8 hours. After cooling to room temperature, an aqueous phase was removed. An organic phase which had been separated was washed with water and saturated brine, and then dried with magnesium sulfate. After the magnesium sulfate was filtered out, the organic phase was concentrated. The resulting residue was purified by means of silica gel column chromatography, whereby 25.0 g (yield: 89%) of 9-(2-formylphenyl)phenanthrene was obtained.

Quelle