Sodium Iodide → HCID 58963157, compound

HRID 917531Notes

Reaction equation

HRID 917531 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][CH3:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C:19](=[O:21])[CH3:20].[I-].[Na+]>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:18][C:19](=[O:21])[CH3:20])=[C:4]([CH2:9][CH3:10])[CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 878774-Bromo-2-ethylphenol

Product 1

HCID 58963157HCID 58963157, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-bromo-2-ethylphenol (72.79 g, 362 mmoles) was dissolved in acetone (1.3 liter) and potassium carbonate (100 g, 724 mmoles) was added. The reaction was stirred for five minutes. Chloroacetone (43.2 ml, 543 mmoles) and sodium iodide (13.6, 90 mmoles) was added and the reaction turned orange upon stirring. The reaction was stirred overnight at room temperature and the solvent removed in vacuo. Ethyl acetate (2.5 l) and water (800 ml) were added. The organic layer was separated, washed with aqueous Na2S2O3, dried over sodium sulfate and filtered. The solvent was removed in vacuo and the crude product run through a plug of silica gel (ca. 500 g) and eluted with 20% ethyl acetate in hexane. The solvent was removed to obtain 95 g of 1-(4-bromo-2-ethylphenoxy)propan-2-one 30.

Workup

  1. stirringupon stirring
  2. stirringThe reaction was stirred overnight at room temperature
  3. customthe solvent removed in vacuo
  4. additionEthyl acetate (2.5 l) and water (800 ml) were added
  5. customThe organic layer was separated
  6. washwashed with aqueous Na2S2O3
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customThe solvent was removed in vacuo
  10. washthe crude product run through a plug of silica gel (ca. 500 g) and eluted with 20% ethyl acetate in hexane
  11. customThe solvent was removed

Sources & evidence

ORD record
ord-cda8c76ca42248e486b357fc713e9031
Source dataset
uspto-grants-2007_09
Patent number
US07273886B2

Reaction notes

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