Dimethyl Sulfoxide → 2,7-Dibromo-9,9-di-n-octylfluorene

HRID 645307Notes

Reaction equation

HRID 645307 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][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[OH-].[Na+].[C:27]1([CH3:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH3:34]S(C)=O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[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)[C:5]([CH2:34][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:27][CH3:33])([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:4]=2[CH:3]=1

Participants

8

Reactant 5

HCID 679Dimethyl SulfoxideHCID 1140TolueneHCID 81401-BromooctaneHCID 14798Sodium HydroxideHCID 1400732,7-Dibromofluorene

Product 1

HCID 52153212,7-Dibromo-9,9-di-n-octylfluoreneYield 79%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

2,7-di bromo fluorene (25 g, 77 mmol), octylbromide (44.7 g, 0.596 mols), sodium hydroxide (37.5 g, 0.937 mols), and tetrabutyl ammonium bromide (0.5 g, 1.55 mmol) were dissolved in dimethyl sulfoxide (75 ml)-water (37.5 ml) mixed solvent. It was kept warm at 80° C. for 6 hours. After cooling, toluene (100 ml) and water (100 ml) were added, and the organic layer was partitioned. The organic layer is washed with water, 3% hydrochloric acid, and water, and then dehydrated with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the crude product was purified by silica-gel chromatography, and 2,7-dibromo-9,9-dioctylfluorene was obtained. (Amount: 26.85 g, yield: 79%)

Workup

  1. additionmixed solvent
  2. temperatureAfter cooling
  3. customthe organic layer was partitioned
  4. washThe organic layer is washed with water, 3% hydrochloric acid, and water
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe crude product was purified by silica-gel chromatography

Sources & evidence

ORD record
ord-aa7caae9fe6a44939a101baec01465c4
Source dataset
uspto-grants-2010_04
Patent number
US07701129B2

Reaction notes

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