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

HRID 11744
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Reaction equation

HRID 11744 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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 (14H, 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.

Workup

  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

Sources & evidence

ORD record
ord-60f1ae2a33014d79b78157a9b7cfbe01
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07098295B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes