Potassium Iodide → Methyl 4-(2-iodoethyl)benzoate

HRID 1512196Notes

Reaction equation

HRID 1512196 reaction equation
Cl[CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1.[I-:14].[K+]>C(#N)C>[I:14][CH2:2][CH2:3][C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4875Potassium IodideHCID 22098587Methyl 4-(2-chloroethyl)benzoate

Product 1

HCID 22639144Methyl 4-(2-iodoethyl)benzoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

70 g (352.4 mmol) of methyl 4-(2-chloroethyl)benzoate [CAS Reg. No. 65787-72-6] and 146.2 g (880.9 mmol) of potassium iodide are suspended in 800 ml of acetonitrile and stirred under reflux for three days. After the reaction has gone to completion, the reaction solution is cooled and filtered, and the filtrate is evaporated to dryness under reduced pressure. The resulting residue is purified by flash chromatography on silica gel (mobile phase: petroleum ether/ethyl acetate 30:1→20:1). This gives 101 g (348.3 mmol, 98.8% of theory) of a yellowish oil.

Workup

  1. temperatureunder reflux for three days
  2. temperaturethe reaction solution is cooled
  3. filtrationfiltered
  4. customthe filtrate is evaporated to dryness under reduced pressure
  5. customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: petroleum ether/ethyl acetate 30:1→20:1)

Sources & evidence

ORD record
ord-73622908ca18476080d1858fe349cd55
Source dataset
uspto-grants-2012_07
Patent number
US08217063B2

Reaction notes

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