2-Iodothiophene → 2,2'-Bithiophene

HRID 1450607Notes

Reaction equation

HRID 1450607 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-e4a6758d59ef48aa9cf5265da52a81fc
Source dataset
uspto-grants-1997_02
Patent number
US05602170

Reaction notes

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