Sodium Iodide → Methyl 3-(2-iodoethoxy)benzoate

HRID 276724Notes

Reaction equation

HRID 276724 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9].[I-:15].[Na+]>CC(C)=O>[I:15][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][CH:14]=1)[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 10491483Methyl 3-(2-bromoethoxy)benzoate

Product 1

HCID 10979673Methyl 3-(2-iodoethoxy)benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of methyl 3-(2-bromoethoxy)-benzoate (2.4 g, 9.26 mmol) and sodium iodide (2.78 g, 18.52 mmol) in acetone (50 mL) is refluxed for 2 hours. The resulting mixture is then filtered and concentrated. The residue is diluted with EtOAc (100 mL), washed with 5% Na2SO3 (50 mL), water (2×50 mL) and brine (50 mL), dried over MgSO4 and evaporated to yield methyl 3-(2-iodoethoxy)-benzoate, as a yellow oil, which is used directly.

Workup

  1. filtrationThe resulting mixture is then filtered
  2. concentrationconcentrated
  3. additionThe residue is diluted with EtOAc (100 mL)
  4. washwashed with 5% Na2SO3 (50 mL), water (2×50 mL) and brine (50 mL)
  5. dry with materialdried over MgSO4
  6. customevaporated

Sources & evidence

ORD record
ord-94db2aa8ea8f4c66b3a6f14781fa2e70
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

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