反応 #1726665

ord-e5b9ffe24bfb4755865481d8a016576f

反応方程式

O=C([O-])[O-].[K+].[K+]
potassium carbonate
Ic1c2ccccc2c(-c2ccccc2)c2ccccc12
9-iodo-10-phenylanthracene
OB(O)c1ccc(Br)cc1
p-bromophenyl boronic acid
Brc1ccc(-c2c3ccccc3c(-c3ccccc3)c3ccccc23)cc1
light-brown solid
収率 52.0%
Brc1ccc(-c2c3ccccc3c(-c3ccccc3)c3ccccc23)cc1
9-(4-bromophenyl)-10-phenylanthracene
収率 52.0%

反応条件

温度
80°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他Into a 50 mL three-neck flask were put
  2. 2
    その他This mixture was degassed under reduced pressure
  3. 3
    ろ過Then, the mixture was subjected to suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina
  4. 4
    洗浄The obtained filtrate was washed with water
  5. 5
    乾燥a saturated saline, and then dried with magnesium sulfate
  6. 6
    ろ過filtered
  7. 7
    濃縮the obtained filtrate was concentrated
  8. 8
    その他to give a solid
  9. 9
    その他The obtained solid was recrystallized with chloroform/hexane

実験手順

Into a 50 mL three-neck flask were put 1.0 g (2.63 mmol) of 9-iodo-10-phenylanthracene and 542 mg (2.70 mmol) of p-bromophenyl boronic acid. The atmosphere in the flask was replaced with nitrogen. After that, 10 mL of toluene and 3 mL of potassium carbonate aqueous solution (2.0 M) were added to the flask. This mixture was degassed under reduced pressure, then 46 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium(0) was added to the mixture. The mixture was stirred under a nitrogen stream at 80° C. for 9 hours. After the stirring, about 20 mL of toluene was added to this mixture. Then, the mixture was subjected to suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina. The obtained filtrate was washed with water and a saturated saline, and then dried with magnesium sulfate. This mixture was gravity filtered, and the obtained filtrate was concentrated to give a solid. The obtained solid was recrystallized with chloroform/hexane to give 0.56 g of a light-brown solid, which was the object of the synthesis, in a yield of 45%.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US08110122B2uspto-grants-2012_02