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1-Bromohexane → 2,7-Dibromo-9,9-dihexyl-9H-fluorene

HRID 1581456
Notes
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Reaction equation

HRID 1581456 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.[CH2:16](Br)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[OH-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[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)[C:5]([CH2:13][CH2:14][CH2:2][CH2:3][CH2:4][CH3:12])([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:4]=2[CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 81011-BromohexaneHCID 14798Sodium HydroxideHCID 1400732,7-Dibromofluorene

Product 1

HCID 35396472,7-Dibromo-9,9-dihexyl-9H-fluoreneYield 179.6%

Reagents, catalysts & solvents 1

HCID 70681Tetrabutylammonium ChlorideCatalyst

Conditions

Temperature
80 °C

Procedure

In a 250 milliliter round bottom flask there was added 2,7-dibromofluorene (6.45 grams), n-hexyl bromide (16.5 grams), tetra-n-butylammonium chloride (0.5 grams), and a 50 weight % aqueous sodium hydroxide solution. The resulting mixture was stirred at 80° C. for 3 hours. After cooling to ambient temperature, about 23° C., the product mixture was transferred to a separatory funnel and extracted with toluene. The toluene extracts were washed with water and dried over anhydrous magnesium sulfate. Removal of the organic solvent by evaporation afforded an oily residue, which was crystallized from ethanol to provide 8.8 grams of 2,7-dibromo-9,9-di-n-hexylfluorene as colorless crystals.

Workup

  1. temperatureAfter cooling to ambient temperature, about 23° C.
  2. customthe product mixture was transferred to a separatory funnel
  3. extractionextracted with toluene
  4. washThe toluene extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customRemoval of the organic solvent
  7. customby evaporation
  8. customafforded an oily residue, which
  9. customwas crystallized from ethanol

Sources & evidence

ORD record
ord-13747d705e2648648e970e77b20a4c63
Source dataset
uspto-grants-2004_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06730417B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes