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

HRID 1057263Notes

Reaction equation

HRID 1057263 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, 0.1mole), 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-dbe30e7065b64b02b7f64b323256eddf
Source dataset
uspto-grants-2003_02
Patent number
US06514632B1

Reaction notes

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