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

HRID 11742

반응식

HRID 11742 반응식
[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

참가 물질

5

반응물 3

HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 110878771,1-Dibromodecane

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-fd7d25416553452abaa8a1d4cd2d080e
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098295B2

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