反応 #91662

ord-dfcc3666a7d64d84adcb20b07e17bb0f

反応方程式

O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
Oc1cccc(Br)c1
3-Bromophenol
OB(O)c1cccnc1
pyridin-3-ylboronic acid
Oc1cccc(-c2cccnc2)c1
3-(pyridin-3-yl)phenol
収率 78.8%

反応条件

温度
120°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他After the completion of the reaction
  2. 2
    ろ過the reaction mixture was filtered
  3. 3
    workup.ADDITIONThe filtrate was added with water
  4. 4
    抽出extracted with ethyl acetate
  5. 5
    乾燥The obtained organic layer was dried over magnesium sulfate
  6. 6
    その他purified by column chromatography (hexane:ethyl acetate=9:1)

実験手順

3-Bromophenol (500 mg, 2.86 mmol) and pyridin-3-ylboronic acid (422 mg, 3.76 mmol) were dissolved in dimethoxyethane/water=5 mL/2.5 mL. Pd(dppf)Cl2 (118 mg, 0.14 mmol) and sodium carbonate (919 mg, 8.67 mmol) were added thereto, followed by stirring in microwave at 120° C. for 20 minutes. After the completion of the reaction, the reaction mixture was filtered using Celite. The filtrate was added with water, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, and purified by column chromatography (hexane:ethyl acetate=9:1) to obtain 3-(pyridin-3-yl)phenol (386 mg, 78%).

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US09447083B2uspto-grants-2016_09