Water → 9,9-dihexylfluorene

HRID 480443Notes

Reaction equation

HRID 480443 reaction equation
[CH:1]1[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].[CH2:20](Br)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].O>O1CCCC1>[CH2:14]([C:12]1([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 6853FluoreneHCID 8058Hexane2×HCID 81011-Bromohexane2×

Product 1

HCID 51284499,9-dihexylfluoreneYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In the stream of dry nitrogen, 5.0 g (30 mmol) of fluorene was dissolved in dry tetrahydrofuran. To this solution, 22 ml (35 mmol) of a 1.6 M hexane solution of n-butylithium was added dropwise at −78° C., and the mixture was stirred at the temperature for 1 hour. To this was then added dropwise 4.9 ml (35 mmol) of n-hexyl bromide, and the mixture was stirred at −78° C. for 1 hour, and then at room temperature for 1 hour. To the resultant, 22 ml (35 mmol) of a 1.6 M hexane solution of n-butylithium was further added dropwise at −78° C., and the mixture was stirred at the temperature for 1 hour. To this was then added dropwise 4.9 ml (35 mmol) of n-hexyl bromide, and the mixture was stirred at −78° C. for 1 hour, and then at room temperature for 1 hour. Water was added dropwise to this mixture with ice-cooling, and the resultant was then subjected to extraction with ethyl acetate. The extract was dehydrated and dried over magnesium sulfate, and the solvent was then distilled off. The residue was subjected to recrystallization from hexane to obtain 9.5 g (95%) of 9,9-dihexylfluorene.

Workup

  1. stirringthe mixture was stirred at −78° C. for 1 hour
  2. waitat room temperature for 1 hour
  3. stirringthe mixture was stirred at the temperature for 1 hour
  4. stirringthe mixture was stirred at −78° C. for 1 hour
  5. waitat room temperature for 1 hour
  6. temperaturecooling
  7. extractionthe resultant was then subjected to extraction with ethyl acetate
  8. dry with materialdried over magnesium sulfate
  9. distillationthe solvent was then distilled off
  10. customThe residue was subjected to recrystallization from hexane

Sources & evidence

ORD record
ord-2fbcf5d7e8d64941b0bf3da9948559e3
Source dataset
uspto-grants-2003_11
Patent number
US06650047B2

Reaction notes

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