2-Iodothiophene → 2,2'-Bithiophene

HRID 1289112Notes

Reaction equation

HRID 1289112 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-36aa96b5e9f740e5aca841d4e4825799
Source dataset
uspto-grants-1998_05
Patent number
US05747525

Reaction notes

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