反応 #1095840

ord-4017f5970f0b41a1af1bac5700e2c726

反応方程式

c1ccc2c(c1)[nH]c1ccccc12
carbazole
II
I2
[Na+].[OH-]
NaOH
O=S(=O)(O)O
H2SO4
Ic1ccc2[nH]c3ccccc3c2c1
compound 1
収率 140.1%
Ic1ccc2[nH]c3ccccc3c2c1
3-Iodocarbazole
収率 140.1%

試薬

なし

反応条件

温度
65°CELSIUS
詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他Ethanol was removed
  2. 2
    抽出the reaction solution was extracted two times with chloroform
  3. 3
    洗浄The extract was washed two times with water
  4. 4
    乾燥The organic phase was dried over Na2SO4
  5. 5
    その他the solvent was removed
  6. 6
    その他The residue was purified by column chromatography (HexH:AcOEt=4:1)

実験手順

To an ethanol solution (500 mL) of carbazole (2.50 g, 15.0 mmol), NaIO4 (0.80 g, 3.75 mmol) and I2 (1.89 g, 7.45 mmol) were sequentially added, and then an ethanol solution (100 mL) of H2SO4 (1.60 mL, 30.0 mmol) was added. The reaction solution was refluxed for one hour at 65° C. The loss of raw materials was confirmed by TLC (HexH:AcOEt=4:1), and an ethanol solution (100 mL) of NaOH (1.4 g) was added thereto to neutralize the system. Ethanol was removed, and then the reaction solution was extracted two times with chloroform. The extract was washed two times with water. The organic phase was dried over Na2SO4, and the solvent was removed. The residue was purified by column chromatography (HexH:AcOEt=4:1), and thus compound 1 (3.06 g, 70%) was obtained as a white powder. Thus, 3,6-diiodocarbazole (0.47 g, 7.5%) was obtained as a white powder.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US07972792B2uspto-grants-2011_07