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

HRID 1636037Notes

Reaction equation

HRID 1636037 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 are stirred vigorously at 80° C. for 1 hour. The reaction mixture is allowed to cool to room temperature and extracted with ether. The ether extracts are washed with water and dried over anhydrous magnesium sulfate. Removal of solvent gives a yellow solid which is 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 shows that the product has a purity of 99.5 percent and the proton and carbon-13 NMR are consistent with the title structure.

Workup

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

Sources & evidence

ORD record
ord-b4691a1d923440be839d85670f9049d0
Source dataset
uspto-grants-2003_01
Patent number
US06512083B1

Reaction notes

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