2,7-Dibromofluorene → 2,7-Dibromo-9,9-bis(6-bromohexyl)-9H-fluorene
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.BrCCOCCO[CH2:23][CH2:24][Br:25]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[K+]>[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]([CH2:8][CH2:7][CH2:6][CH2:5][CH2:23][CH2:24][Br:25])([CH2:10][CH2:11][CH2:12][CH2:4][CH2:3][CH2:2][Br:1])[C:4]=2[CH:3]=1Participants
5
Procedure
2,7-Dibromofluorene (1.23 g, 5 mmol) was added to a mixture of aqueous potassium hydroxide (100 mL, 50 w %), tetrabutylammonium bromide (0.330 g, 1 mmol), and 1,2-bis(2-bromoethoxy)ethane (13.9 g, 50 mmol) at 75° C. After 15 min, the mixture was cooled to room temperature. After extraction with CH2Cl2, the combined organic layers were washed successively with water, aqueous HCl (1 M), water, and brine and then dried over Na2SO4. After removal of the solvent and the excess 1,2-bis(2-bromoethoxy)ethane; the residue was purified by silica gel column chromatography using hexane and dichloromethane (1:2) as the eluent, and recrystallized from ethanol and CH2Cl2 (5:1) to afford M2 as white needle crystals (1.50 g, 48.0%).
Workup
- extractionAfter extraction with CH2Cl2
- washthe combined organic layers were washed successively with water, aqueous HCl (1 M), water, and brine
- dry with materialdried over Na2SO4
- customAfter removal of the solvent
- customthe residue was purified by silica gel column chromatography
- customrecrystallized from ethanol and CH2Cl2 (5:1)
Sources & evidence
- ORD record
- ord-bac7c351e84844bc9c7d01b51860fdac
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08507290B2
Reaction notes
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