2,2'-Bithiophene → 5-Iodo-2,2'-bithiophene

HRID 1291581Notes

Reaction equation

HRID 1291581 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:7][CH:8]=[CH:9][CH:10]=1.[I:11]I.CCO>C(O)C>[I:11][C:5]1[S:1][C:2]([C:6]2[S:7][CH:8]=[CH:9][CH:10]=2)=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 681202,2'-BithiopheneHCID 131719860I2 EtOH

Product 1

HCID 113237785-Iodo-2,2'-bithiopheneYield 186.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

33.2 g of 2,2'-bithiophene was dissolved in 50 ml of ethanol and I2 /EtOH (20.3 g/220 ml) was added. Then HIO3 /H2O (12 g/20 ml) were added slowly during 2 hours with stirring. The mixture was stirred for further 3 hours and the ethanol was evaporated. The residue was extracted with dichloromethane and dried over anhydrous magnesium sulfate. After the solvent was removed, the crude product was vacuum distilled to give 5-iodo-2,2'-bithiophene 36.8 g (105°-110° C./0.1 mm-Hg). The yield is 65-70%. The residue was purified by silica column chromatography and yielded 5.36 g of 5,5'-diiodo-2,2'-bithiophene (6.4%) with melting point of 170° C.

Workup

  1. stirringThe mixture was stirred for further 3 hours
  2. customthe ethanol was evaporated
  3. extractionThe residue was extracted with dichloromethane
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the solvent was removed
  6. distillationdistilled

Sources & evidence

ORD record
ord-c6073b55a80b41dc91ed0fcf30645559
Source dataset
uspto-grants-1998_05
Patent number
US05753692

Reaction notes

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