2-Iodothiophene → 2,2'-Bithiophene

HRID 1291574Notes

Reaction equation

HRID 1291574 reaction equation
I[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1>CN(C=O)C>[S:3]1[CH:4]=[CH:5][CH:6]=[C:2]1[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1

Participants

3

Reactant 1

HCID 189212-Iodothiophene

Product 1

HCID 681202,2'-BithiopheneYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

21 g of 2-iodo-thiophene was dissolved in 50 ml of DMF in 3-necks-bottle (250 ml). 10 g of Cu powder was then added into the solution and refluxed for 15 hours. Then the solution was filtered and the DMF was removed under reduced pressure. The crude product was further purified by column chromatography and both 2,2'-bithiophene (97%) as well as 2,2':5',2"-terthiophene (2%) were obtained.

Workup

  1. temperaturerefluxed for 15 hours
  2. filtrationThen the solution was filtered
  3. customthe DMF was removed under reduced pressure
  4. customThe crude product was further purified by column chromatography

Sources & evidence

ORD record
ord-87b2e6577d3a4f84af22637ddaf34a8d
Source dataset
uspto-grants-1998_05
Patent number
US05753692

Reaction notes

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