Sodium Iodide → Iodomethyl Benzoate

HRID 2401193Notes

Reaction equation

HRID 2401193 reaction equation
[C:1]([O:9][CH2:10]Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:12].[Na+]>C(#N)C.O>[C:1]([O:9][CH2:10][I:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 79257Chloromethyl benzoate

Product 1

HCID 10015543Iodomethyl BenzoateYield 71.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Chloromethyl benzoate (2.87 g, 16.82 mmol) was dissolved in acetonitrile (20 mL) and treated portionwise with sodium iodide (5.04 g, 33.6 mmol). The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (×2). The ethyl acetate layers were combined, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Biotage SP4) eluting with a gradient of 0-20% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as a yellow oil (3.15 g);

Workup

  1. extractionextracted with ethyl acetate (×2)
  2. customdried under magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by column chromatography (Biotage SP4)
  5. washeluting with a gradient of 0-20% ethyl acetate and iso-hexane
  6. additionProduct containing fractions
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-08f072f24cdd4520a94b8a11359c627c
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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