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

HRID 11742

反応式

HRID 11742 の反応式
[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

参加物

5

反応物 3

HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 110878771,1-Dibromodecane

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fd7d25416553452abaa8a1d4cd2d080e
出典データセット
uspto-grants-2006_08
特許番号
US07098295B2

関連ノート

読み込み中…