تفاعل #1095840

ord-4017f5970f0b41a1af1bac5700e2c726

معادلة التفاعل

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

المتفاعلات

الكواشف

لا شيء

ظروف التفاعل

درجة الحرارة
65°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىEthanol was removed
  2. 2
    استخلاصthe reaction solution was extracted two times with chloroform
  3. 3
    غسيلThe extract was washed two times with water
  4. 4
    تجفيفThe organic phase was dried over Na2SO4
  5. 5
    أخرىthe solvent was removed
  6. 6
    أخرىThe residue was purified by column chromatography (HexH:AcOEt=4:1)

الإجراء التجريبي

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.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US07972792B2uspto-grants-2011_07