6-Bromo-1-hexene → HCID 57980924, compound

HRID 1868000Notes

Reaction equation

HRID 1868000 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.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22]>C1(C)C=CC=CC=1.[OH-].[Na+].[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-]>[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]([CH2:12][CH2:13][CH2:14][CH2:2][CH:3]=[CH2:4])([CH2:17][CH2:18][CH2:19][CH2:20][CH:21]=[CH2:22])[C:4]=2[CH:3]=1

Participants

6

Reactant 2

HCID 759066-Bromo-1-hexeneHCID 1400732,7-Dibromofluorene

Product 1

HCID 57980924HCID 57980924, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

2,7-dibromofluorene (5 g, 15.4 mmol) was combined with 1-bromo-5-hexene (7.5 g, 46.0 mmol) in toluene (50 mL), NaOH (50 mL, 50%, aq) and Bu4NBr (0.1 g) as a phase transfer catalyst. The mixture was heated at ca. 100° C. with stirring for 5 h. The organic layer was separated from the aqueous layer and then treated with 10% HCl and then water and then stirred the MgSO4 and carbon black. The solution was filtered and all solvents were removed in vacuo to give a brown oil, 7.83 g.

Workup

  1. customThe organic layer was separated from the aqueous layer
  2. additiontreated with 10% HCl
  3. stirringwater and then stirred the MgSO4 and carbon black
  4. filtrationThe solution was filtered
  5. customall solvents were removed in vacuo
  6. customto give a brown oil, 7.83 g

Sources & evidence

ORD record
ord-36db5b05e3224e1292713a29346191eb
Source dataset
uspto-grants-2009_12
Patent number
US07633220B2

Reaction notes

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