1,6-Dibromohexane → 2,7-Dibromo-9,9-bis(6-bromohexyl)-9H-fluorene

HRID 857269Notes

Reaction equation

HRID 857269 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Br:8].[Br:9][C:10]1[CH:22]=[CH:21][C:20]2[C:19]3[C:14](=[CH:15][C:16]([Br:23])=[CH:17][CH:18]=3)[CH2:13][C:12]=2[CH:11]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[K+]>[Br:9][C:10]1[CH:22]=[CH:21][C:20]2[C:19]3[C:14](=[CH:15][C:16]([Br:23])=[CH:17][CH:18]=3)[C:13]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Br:8])([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][Br:8])[C:12]=2[CH:11]=1

Participants

5

Reactant 2

HCID 123681,6-DibromohexaneHCID 1400732,7-Dibromofluorene

Product 1

HCID 218679302,7-Dibromo-9,9-bis(6-bromohexyl)-9H-fluoreneYield 80%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 14797Potassium HydroxideSolvent

Procedure

To a mixture of tetrabutylammonium bromide (300 mg, 9.3 mmol), aqueous potassium hydroxide (100 mL, 50%) and 1,6-dibromohexane (22.6 g, 92.6 mmol) was added 2,7-dibromofluorene at 75° C. After 15 minutes, the mixture was cooled down to room temperature, and extracted with CH2Cl2. The organic layer was washed with water, aqueous HCl, water and brine, dried over MgSO4, and then concentrated. Unreacted 1,6-dibromohexane was distilled off. The residue was purified by silica gel column chromatography (Hexane:CHCl3=9:1) and recrystallized from ethanol to give 2 (4.8 g, 80%) as a white solid. 1H NMR (200 MHz, CDCl3): δ 7.2–7.4 (m, 6H), 3.12 (t, 4H), 1.75 (t, 4H), 1.5 (m, 4H), 1.0 (m, 8H), 0.4 (m, 4H). 13C NMR (50 MHz, CDCl3): δ 152.3, 139.2, 130.5, 126.2, 121.7, 121.4, 55.7, 40.2, 34.1, 32.8, 29.1, 27.9, 23.6.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with water, aqueous HCl, water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. distillationUnreacted 1,6-dibromohexane was distilled off
  6. customThe residue was purified by silica gel column chromatography (Hexane:CHCl3=9:1)
  7. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-d8fefa1c433247eeab68944dfe570952
Source dataset
uspto-grants-2006_12
Patent number
US07144950B2

Reaction notes

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