9-(2-bromoethyl)-9H-fluorene → HCID 86752827, compound

HRID 1106956

Reaction equation

HRID 1106956 reaction equation
[CH:1]([C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2[CH:4]=1)=[CH2:2].C([Li])CCC.Br[CH2:22][CH2:23][CH:24]1[C:36]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2>C(OCC)C>[CH:1]([C:3]1[CH:15]=[CH:14][C:13]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6][C:5]=2[C:4]=1[C:24]1([CH2:23][CH3:22])[C:36]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=2[C:30]2[C:25]1=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH2:2]

Participants

5

Reactant 3

HCID 110002159-(2-bromoethyl)-9H-fluoreneHCID 110416072-ethenyl-9H-fluoreneHCID 178418339Butyllithium

Product 1

HCID 86752827HCID 86752827, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 1.15 g (6.0 mmol) 2-vinylfluorene in 100 mL diethyl ether was added 3.75 mL (6.0 mmol) n-butyllithium (1.6M in hexane). The reaction mixture was stirred for 4 hours at room temperature. Then 1.64 g (6.0 mmol) 1-bromo-2-(9-fluorenyl)ethane was added and the mixture was stirred for 14 hours at room temperature. The precipitate was removed by filtration, washed with methanol, filtered with pentane using silica gel 60, and concentrated by evaporation under vacuum. The yield was 1.69 g (73%) 1-(9-(2-vinyl)fluorenyl)-2-(9-fluorenyl)ethane as a colorless solid.

Workup

  1. stirringthe mixture was stirred for 14 hours at room temperature
  2. customThe precipitate was removed by filtration
  3. washwashed with methanol
  4. filtrationfiltered with pentane
  5. concentrationconcentrated by evaporation under vacuum

Sources & evidence

ORD record
ord-99492908cd3e47c597a9cb4c40d1c93d
Source dataset
uspto-grants-2000_05
Patent number
US06057410

Linked notes

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