反応 #155678

反応方程式

sodium carbonate

phenanthrene-2-boronic acid

4-bromoiodobenzene

→

10-(3-bromophenyl)benzo[c]phenanthrene

収率 158.1%

溶媒

toluene

反応条件

後処理

1. 1
   温度under reflux
2. 2
   抽出the reaction solution was extracted with toluene
3. 3
   その他The water layer was removed
4. 4
   洗浄the organic layer was sequentially washed with water
5. 5
   乾燥a saturated salt solution, and was then dried with magnesium sulfate
6. 6
   その他After magnesium sulfate had been separated by filtration
7. 7
   濃縮the organic layer was concentrated
8. 8
   その他The residue was purified by silica gel column chromatography

実験手順

Under an argon atmosphere, 22.2 g of phenanthrene-2-boronic acid, 28.3 g of 4-bromoiodobenzene, 2.31 g of tetrakis(triphenyl phosphine) palladium(0), 400 mL of toluene, and 200 mL of a 2-M aqueous solution of sodium carbonate were loaded, and then the mixture was stirred for 8 hours under reflux. After having been cooled to room temperature, the reaction solution was extracted with toluene. The water layer was removed, and the organic layer was sequentially washed with water and a saturated salt solution, and was then dried with magnesium sulfate. After magnesium sulfate had been separated by filtration, the organic layer was concentrated. The residue was purified by silica gel column chromatography. Thus, 30.3 g of 10-(3-bromophenyl)benzo[c]phenanthrene were obtained (91%).

出典