反応 #1483121

反応方程式

9-bromophenanthrene

2-formylphenylboronic acid

sodium carbonate

→

9-(2-formylphenyl)phenanthrene

収率 89.0%

溶媒

dimethyl ether

反応条件

後処理

1. 1
   温度the resultant was refluxed
2. 2
   温度while heating for 8 hours
3. 3
   その他an aqueous phase was removed
4. 4
   その他An organic phase which had been separated
5. 5
   洗浄was washed with water and saturated brine
6. 6
   乾燥dried with magnesium sulfate
7. 7
   ろ過After the magnesium sulfate was filtered out
8. 8
   濃縮the organic phase was concentrated
9. 9
   その他The resulting residue was purified by means of silica gel column chromatography

実験手順

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.

出典