N-Iodosuccinimide → 2-(4-Fluorobenzyl)-5-iodothiophene

HRID 1720433Notes

Reaction equation

HRID 1720433 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[I:14]N1C(=O)CCC1=O.C(Cl)(Cl)Cl.C(O)(=O)C>O>[I:14][C:11]1[S:10][C:9]([CH2:8][C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 105839052-[(4-Fluorophenyl)methyl]thiopheneHCID 21584526Acetic acid chloroform

Product 1

HCID 106154672-(4-Fluorobenzyl)-5-iodothiopheneYield 95.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(4-fluorophenylmethyl)thiophene (3.85 g, 20.0 mmol), prepared as described in step 1, and N-iodosuccinimide (4.50 g, 20.0 mmol) in 1:1 chloroform-acetic acid (40 mL) was stirred at ambient temperature for 1 hour and then diluted with an equal volume of water. The organic layer was washed with saturated aqueous NaHCO3 solution (2×50 mL), 10% aqueous sodium thiosulfate solution (2×50 mL) and once with brine. After drying over MgSO4, the organic layer was concentrated in vacuo to give 6.07 g (95%) of 2-iodo-5-(4-fluorophenylmethyl)thiophene as a gold colored oil.

Workup

  1. customprepared
  2. washThe organic layer was washed with saturated aqueous NaHCO3 solution (2×50 mL), 10% aqueous sodium thiosulfate solution (2×50 mL) and once with brine
  3. dry with materialAfter drying over MgSO4
  4. concentrationthe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-3015811dad19412bac3622d39304a85d
Source dataset
uspto-grants-1996_04
Patent number
US05506261

Reaction notes

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