Carbazole → 9-(10-Bromodecyl)-9H-carbazole

HRID 1353029Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1353029
[H-].[Na+].[CH:3]1[C:15]2[NH:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[Br:16][CH:17](Br)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C1COCC1>[Br:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][N:14]1[C:13]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:7]2[C:15]1=[CH:3][CH:4]=[CH:5][CH:6]=2

Komponenten

5

Edukt 3

HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 110878771,1-Dibromodecane

Produkt 1

HCID 219763109-(10-Bromodecyl)-9H-carbazole

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

10 g (0.25 mol) sodium hydride (60%) was added in several portions into a solution of 30.6 g (0.20 mol) carbazole in 200 mL THF. Then the mixture was transferred into a funnel from which it was added dropwisely into a solution of 180 g (0.6 mol) dibromodecane in 500 mL THF at 70° C. and the mixture was refluxed for 48 h. After cooling, it was filtered. The filtrate was distilled in order to remove remaining dibromodecane. The residue was diluted with water and extracted with CH2Cl2. The organics was washed with brine and dried over anhydrous MgSO4 overnight. After removed the solvent by rotary evaporator, it was purified by silica chromography to give 31.6 g (41%, yield, mp 38˜40° C.) white solid product. 1H NMR (500 MHz, CDCl3), δ (ppm): 8.14 (2H, d), 7.51 (2H, d), 7.44 (2H, d), 7.26 (2H, d), 4.30 (2H, t), 3.41 (2H, t), 1.27˜1.90 (16H, m).

Aufarbeitung

  1. customThen the mixture was transferred into a funnel from which it
  2. temperaturethe mixture was refluxed for 48 h
  3. temperatureAfter cooling
  4. filtrationit was filtered
  5. distillationThe filtrate was distilled in order
  6. customto remove
  7. additionThe residue was diluted with water
  8. extractionextracted with CH2Cl2
  9. washThe organics was washed with brine
  10. dry with materialdried over anhydrous MgSO4 overnight
  11. customAfter removed the solvent
  12. customby rotary evaporator, it
  13. customwas purified by silica chromography
  14. customto give
  15. custom31.6 g (41%, yield, mp 38˜40° C.) white solid product

Quellen und Nachweise

ORD-Eintrag
ord-85b58370d83e4597a0f8262c3092ff82
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07220819B2

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