Butyl bromide → 2,7-Dibromo-9,9-dibutyl-9H-fluorene

HRID 1383704Notes

Reaction equation

HRID 1383704 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][CH3:19].[OH-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:16]([C:5]1([CH2:14][CH2:2][CH2:3][CH3:4])[C:4]2[CH:3]=[C:2]([Br:1])[CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][C:8]([Br:15])=[CH:9][CH:10]=2)[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 8002Butyl bromideHCID 14798Sodium HydroxideHCID 1400732,7-Dibromofluorene

Product 1

HCID 224758932,7-Dibromo-9,9-dibutyl-9H-fluoreneYield 192.6%

Reagents, catalysts & solvents 1

HCID 70681Tetrabutylammonium ChlorideCatalyst

Procedure

2,7-Dibromofluorene (32.4 g, 0.1 mole), n-butyl bromide (75 g, 0.55 mole), tetra-n-butylammonium chloride (1.5 g) and 50 percent aqueous NaOH solution were stirred vigorously at 80° C. for 1 hour. The reaction mixture was allowed to cool to room temperature and extracted with ether. The ether extracts were washed with water and dried over anhydrous magnesium sulfate. Removal of solvent gave a yellow solid which was recrystallized from 400 mL of ethanol to provide 9,9-di-n-butyl-2,7-dibromofluorene as colorless crystals (42 g, 96 percent yield), melting point 120.5° C. to 121.5° C. HPLC analysis showed that the product had a purity of 99.5 percent and the proton and carbon-13 NMR were consistent with the title structure.

Workup

  1. extractionextracted with ether
  2. washThe ether extracts were washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customRemoval of solvent
  5. customgave a yellow solid which
  6. customwas recrystallized from 400 mL of ethanol

Sources & evidence

ORD record
ord-2d52ed845e6d4f1abbe071b46f13727c
Source dataset
uspto-grants-2001_07
Patent number
US06255447B1

Reaction notes

Loading…