1-Bromohexane → 9,9-Dihexyl-2,7-dibromofluorene

HRID 1581456Notes

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][CH3:21].[OH-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[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]([CH2:13][CH2:14][CH2:2][CH2:3][CH2:4][CH3:12])([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

In a 250 milliliter round bottom flask there was added 2,7-dibromofluorene (6.45 grams), n-hexyl bromide (16.5 grams), tetra-n-butylammonium chloride (0.5 grams), and a 50 weight % aqueous sodium hydroxide solution. The resulting mixture was stirred at 80° C. for 3 hours. After cooling to ambient temperature, about 23° C., the product mixture was transferred to a separatory funnel and extracted with toluene. The toluene extracts were washed with water and dried over anhydrous magnesium sulfate. Removal of the organic solvent by evaporation afforded an oily residue, which was crystallized from ethanol to provide 8.8 grams of 2,7-dibromo-9,9-di-n-hexylfluorene as colorless crystals.

Workup

temperatureAfter cooling to ambient temperature, about 23° C.
customthe product mixture was transferred to a separatory funnel
extractionextracted with toluene
washThe toluene extracts were washed with water
dry with materialdried over anhydrous magnesium sulfate
customRemoval of the organic solvent
customby evaporation
customafforded an oily residue, which
customwas crystallized from ethanol

Sources & evidence

ORD record: ord-13747d705e2648648e970e77b20a4c63
Source dataset: uspto-grants-2004_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06730417B2

Reaction notes

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