Indene → 1-bromo-2-(3-indenyl)ethane

HRID 2216714Notes

Reaction equation

HRID 2216714 reaction equation
[Li]CCCC.CCCCCC.[CH2:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13]1.C1([Li])C2C(=CC=CC=2)C=C1.[Br:31][CH2:32][CH2:33]Br.[NH4+].[Cl-]>CCOCC>[Br:31][CH2:32][CH2:33][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH:13]=1

Participants

8

Reactant 6

HCID 7219IndeneHCID 78391,2-DibromoethaneHCID 8058HexaneHCID 25517Ammonium ChlorideHCID 178418339ButyllithiumHCID 178506815HCID 178506815, compound

Product 1

HCID 121780961-bromo-2-(3-indenyl)ethane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 1.6 M n-BuLi solution in hexane (100 mL, 0.16 mol) was added at 0° C. to a solution of indene (18.6 g, MW=116.16, 0.16 mol) in 300 mL of ether. The resulting suspension was allowed to warm to room temperature and stirred for 4 h at the same temperature. Then the indenyl lithium suspension was cooled again to −50° C. and added of a solution of 1,2-dibromoethane (0.24 mol, 21 mL) in 50 mL of ether. The reaction mixture was allowed to warm up slowly to room temperature and stirred overnight. Then it was treated with a saturated aqueous solution of NH4Cl. The organic phase was isolated, evaporated off to dryness and distilled in vacuo, b.p. 110° C./0.5 torr. Yield 21.6 g (60%). The title compound was characterized by NMR spectroscopy.

Workup

  1. temperatureto warm up slowly to room temperature
  2. stirringstirred overnight
  3. customThe organic phase was isolated
  4. customevaporated off to dryness
  5. distillationdistilled in vacuo, b.p. 110° C./0.5 torr

Sources & evidence

ORD record
ord-5861359191624f4b91ecedfef35fa3d3
Source dataset
uspto-grants-2006_09
Patent number
US07112638B2

Reaction notes

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