Iodine → 5-Iodo-2,2'-bithiophene

HRID 1599497Notes

Reaction equation

HRID 1599497 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.[I+3]=O>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

5

Reactant 3

HCID 807IodineHCID 681202,2'-BithiopheneHCID 178526215HCID 178526215, compound

Product 1

HCID 113237785-Iodo-2,2'-bithiopheneYield 157.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

To a solution of 2,2'-bithiophene (33.2 g) in ethanol (50 ml) was added iodine (20.3 g) in ethanol (200 ml). Then iodine (V) oxide (6.7 g) in ethanol (30 ml) was added dropwisely. The reaction mixture was further stirred at room temperature for 5 hours. Ethanol was removed and the residue was dissolved in dichloromethane. The solution was washed with sodium bicarbonate aqueous solution (10%, 150 ml×2) then water (200 ml×2). Dried over anhydrous magnesium sulfate and concentrated to give crude products. Distilled under vacuum (105°-110° C./0.1 mm Hg) to give 5-iodo-2,2'-bithiophene (36.8 g, 63%). The residue was then separated by silica gel chromatography eluted with n-hexane to give 5,5'-diiodo-2,2'-bithiophene (5.36 g, 6.4%), melting point 170° C.

Workup

  1. customEthanol was removed
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe solution was washed with sodium bicarbonate aqueous solution (10%, 150 ml×2)
  4. dry with materialDried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give crude products
  7. distillationDistilled under vacuum (105°-110° C./0.1 mm Hg)

Sources & evidence

ORD record
ord-9d8c773f33464bc38cf0362e2e42f695
Source dataset
uspto-grants-1998_04
Patent number
US05741811

Reaction notes

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