Reaction #1483121

Reaction equation

9-bromophenanthrene

2-formylphenylboronic acid

sodium carbonate

→

9-(2-formylphenyl)phenanthrene

Yield 89.0%

Solvents

dimethyl ether

Conditions

Workup

1. 1
   Temperaturethe resultant was refluxed
2. 2
   Temperaturewhile heating for 8 hours
3. 3
   Otheran aqueous phase was removed
4. 4
   OtherAn organic phase which had been separated
5. 5
   Washwas washed with water and saturated brine
6. 6
   Dryingdried with magnesium sulfate
7. 7
   FiltrationAfter the magnesium sulfate was filtered out
8. 8
   Concentrationthe organic phase was concentrated
9. 9
   OtherThe resulting residue was purified by means of silica gel column chromatography

Procedure

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.

Source