Sodium Iodide → Tert-butyl 2-iodoacetate

HRID 440632Notes

Reaction equation

HRID 440632 reaction equation
Cl[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[I-:10].[Na+]>CC(C)=O>[I:10][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 66052tert-Butyl chloroacetate

Product 1

HCID 11021060Tert-butyl 2-iodoacetateYield 77.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of t-butyl chloroacetate (20 g) and sodium iodide (25 g) is stirred in acetone (200 ml) for twenty hours. The acetone is removed by distillation under reduced pressure. The residue is partitioned between diethyl ether (100 ml) and water (50 ml). The ether layer is washed with water, 5% sodium thiosulfate solution, and water. The organic layer is dried over sodium sulfate, and evaporated under reduced pressure. There is obtained 25 grams of t-butyl iodoacetate. NMR: 63.5, 1.38.

Workup

  1. customThe acetone is removed by distillation under reduced pressure
  2. customThe residue is partitioned between diethyl ether (100 ml) and water (50 ml)
  3. washThe ether layer is washed with water, 5% sodium thiosulfate solution, and water
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-3fe4f992b9eb42fb843d2e30f01bb3f4
Source dataset
uspto-grants-1996_05
Patent number
US05521103

Reaction notes

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