Sodium Iodide → 2-[1-(2,5-Dichlorophenoxy)-4-iodobutyl]thiophene

HRID 352110Notes

Reaction equation

HRID 352110 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH:5]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[O:6][C:7]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:8]=1[Cl:14].[I-:20].[Na+]>CC(C)=O>[Cl:14][C:8]1[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:7]=1[O:6][CH:5]([C:15]1[S:16][CH:17]=[CH:18][CH:19]=1)[CH2:4][CH2:3][CH2:2][I:20]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 227151352-[4-Chloro-1-(2,5-dichlorophenoxy)butyl]thiophene

Product 1

HCID 227151002-[1-(2,5-Dichlorophenoxy)-4-iodobutyl]thiopheneYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-[4-Chloro-1-(2,5-dichlorophenoxy)butyl]thiophene (2.4 g, 7.1 mmol) was dissolved in a saturated solution of sodium iodide in acetone (200 ml) and the reaction refluxed for 20 hours. The reaction mixture was cooled and the solid filtered off. The filtrate was evaporated in vacuo and the residue taken up in water (50 ml). The mixture was extracted with diethyl ether (3×70 ml) and the combined organic portions were washed with water (3×30 ml), dried (magnesium sulphate), filtered and evaporated in vacuo to give the title compound as a pale straw coloured oil (2.91 g, 95%).

Workup

  1. temperaturethe reaction refluxed for 20 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationthe solid filtered off
  4. customThe filtrate was evaporated in vacuo
  5. extractionThe mixture was extracted with diethyl ether (3×70 ml)
  6. washthe combined organic portions were washed with water (3×30 ml)
  7. dry with materialdried (magnesium sulphate)
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-69960454100b48cfb073fa3355c7f2ef
Source dataset
uspto-grants-2004_06
Patent number
US06743939B2

Reaction notes

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