Sodium Iodide → 5-Iodo-3-methyl-2-(4-propylbenzyl)thiophene

HRID 1469200Notes

Reaction equation

HRID 1469200 reaction equation
Br[C:2]1[S:6][C:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)=[C:4]([CH3:17])[CH:3]=1.[I-:18].[Na+].CNCCNC>O1CCOCC1.[Cu]I>[I:18][C:2]1[S:6][C:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH3:16])=[CH:10][CH:9]=2)=[C:4]([CH3:17])[CH:3]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 8070N,N'-DimethylethylenediamineHCID 666908445-Bromo-3-methyl-2-(4-propylbenzyl)thiophene

Product 1

HCID 666907675-Iodo-3-methyl-2-(4-propylbenzyl)thiopheneYield 96%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a mixture of 5-bromo-3-methyl-2-(4-propylbenzyl)thiophene (46, 0.86 g, 2.77 mmol), sodium iodide (0.83 g, 5.53 mmol) and copper(I) iodide (0.053 g, 0.277 mmol) in dioxane (5.2 mL) was added N,N′-dimethylethylenediamine (0.060 mL, 0.553 mmol). The resulting mixture was heated to 110° C. and stirred for 16 hours. After cooling to room temperature, the reaction mixture was filtered through a plug of Celite® and then washed with EtOAc (50 mL). The filtrate was washed with brine and dried over MgSO4. The organic phase was evaporated under vacuum to provide 5-iodo-3-methyl-2-(4-propylbenzyl)thiophene 47 (0.95 g, 2.66 mmol, 96%) as a yellow oil, which was used without further purification.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe reaction mixture was filtered through a plug of Celite®
  3. washwashed with EtOAc (50 mL)
  4. washThe filtrate was washed with brine
  5. dry with materialdried over MgSO4
  6. customThe organic phase was evaporated under vacuum

Sources & evidence

ORD record
ord-4f0cd076c9a14f19a2727cb63893b40c
Source dataset
uspto-grants-2015_04
Patent number
US09006187B2

Reaction notes

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