N-Iodosuccinimide → 2-Iodo-3-(4fluorophenylmethyl)thiophene

HRID 52188Notes

Reaction equation

HRID 52188 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)=[CH:4][CH:3]=1.C(Cl)(Cl)Cl.CO.[I:20]N1C(=O)CCC1=O>C(Cl)Cl>[I:20][C:10]1[S:11][CH:12]=[CH:13][C:9]=1[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 199633023-(4-Fluorophenylmethyl)thiopheneHCID 21584188Chloroform methanol

Product 1

HCID 199632792-Iodo-3-(4fluorophenylmethyl)thiopheneYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(4-fluorophenylmethyl)thiophene (1.16 g, 6.04 mmol) in 1:1 CHCl3 /methanol was added N-iodosuccinimide (1.70 g, 7.53 mmol). The reaction mixture was stirred for 3 hours, and then was diluted with CH2Cl2. The organic phase was extracted with saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered, and concentrated in vacuo to give 1.83 g of 2-iodo-3-(4fluorophenylmethyl)thiophene which was used without further purification.

Workup

  1. extractionThe organic phase was extracted with saturated aqueous NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-76414163d6a84d8b834fadd2b1086ec7
Source dataset
uspto-grants-1997_04
Patent number
US05616596

Reaction notes

Loading…