Sodium hydride → 9,9-Bis(N-carbazolyl-decyl)-2,7-dibromofluorene

HRID 1353031

反応式

HRID 1353031 の反応式
[Br:1][C:2]1[CH:14]=[CH:13][C:12]2[C:11]3[C:6](=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=3)[CH2:5][C:4]=2[CH:3]=1.[H-].[Na+].Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29]1[C:41]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[C:35]2[C:30]1=[CH:31][CH:32]=[CH:33][CH:34]=2>C1COCC1>[CH:40]1[C:41]2[N:29]([CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:5]3([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][N:29]4[C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][C:35]=5[C:36]5[C:41]4=[CH:40][CH:39]=[CH:38][CH:37]=5)[C:4]4[CH:3]=[C:2]([Br:1])[CH:14]=[CH:13][C:12]=4[C:11]4[C:6]3=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=4)[C:30]3[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:36]=2[CH:37]=[CH:38][CH:39]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 1400732,7-DibromofluoreneHCID 219763109-(10-Bromodecyl)-9H-carbazole

生成物 1

HCID 210441289,9-Bis(N-carbazolyl-decyl)-2,7-dibromofluorene収率 34.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a mixture of 5.2 g (16 mmol) 2,7-dibromofluorene in 300 mL THF was added 1.3 g (41 mmol) sodium hydride (75%) in several portions. A mixture of 15 g (39 mol) N-(10-bromodecyl)-carbazole (8) in 100 mL THF was added dropwisely at 70° C. and the mixture was refluxed for 48 h. After cooling, the solid was filtered and the filtrate was concentrated and dilute with water and extracted with CH2Cl2. The organic layer was collected and washed with brine and dried with anhydrous MgSO4. The crude product was further purified by silica column chromography to give 5.1 g (yield 34%, mp 94˜96° C.) title product. 1H NMR (CDCl3), δ (ppm): 8.10 (4H, d), 7.38˜7.48 (14 H, m), 7.23 (4H, t), 4.27 (4H, t), 0.88˜1.86 (36H, m). Anal. Calcd: C, 73.22; H, 6.68; N, 3.00. Found: C, 72.58; H, 6.59; N, 2.73.

後処理

  1. additionwas added dropwisely at 70° C.
  2. temperaturethe mixture was refluxed for 48 h
  3. temperatureAfter cooling
  4. filtrationthe solid was filtered
  5. concentrationthe filtrate was concentrated
  6. additiondilute with water
  7. extractionextracted with CH2Cl2
  8. customThe organic layer was collected
  9. washwashed with brine
  10. dry with materialdried with anhydrous MgSO4
  11. customThe crude product was further purified by silica column chromography

出典と根拠

ORDレコード
ord-2d60f307539c4c0c9c21aec458cb0ea1
出典データセット
uspto-grants-2007_05
特許番号
US07220819B2

関連ノート

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