Water → 9-n-Hexylfluorene

HRID 1353028

Reaction equation

HRID 1353028 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.C([Li])CCC.[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].O>C1COCC1>[CH2:19]([CH:12]1[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)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 6853FluoreneHCID 81011-BromohexaneHCID 178418339Butyllithium

Product 1

HCID 64278799-n-HexylfluoreneYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-50 °C

Procedure

To a solution of fluorene (33.2 g, 0.20 mol) in 300 mL THF at −78° C., n-butyllithium (2.5 M, 80 mL) was added dropwisely. The mixture was stirred at −50° C. for 45 minutes, and then cooled to −78° C. again and n-hexylbromide (33.0 g, 0.20 mol) in THF (25 mL) was added dropwise to the mixture. The solution was allowed to warm up to room temperature and stirred for 5 h. The mixture was then poured into water and extracted with ether. The organic extracts were washed with brine and dried over magnesium sulfate, and purified by silica gel column with hexane to give pure compound 2 (38 g, yield 76%).

Workup

  1. temperaturecooled to −78° C. again
  2. temperatureto warm up to room temperature
  3. stirringstirred for 5 h
  4. extractionextracted with ether
  5. washThe organic extracts were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. custompurified by silica gel column with hexane

Sources & evidence

ORD record
ord-55fc9f89819045189c01112a2f99cb05
Source dataset
uspto-grants-2007_05
Patent number
US07220819B2

Linked notes

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