Sodium Iodide → HCID 76672298, compound

HRID 2363021Notes

Reaction equation

HRID 2363021 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[CH2:5][CH2:6][CH2:7]Cl.[I-:16].[Na+]>CC(C)=O>[CH3:1][O:2][N:3]=[C:4]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)[CH2:5][CH2:6][CH2:7][I:16]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 76672293HCID 76672293, compound

Product 1

HCID 76672298HCID 76672298, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Chloro-1-(4-fluorophenyl)butan-1-one O-methyl oxime (0.78 g, 3.40 mmol) and sodium iodide (0.76 g, 5.09 mmol) in acetone (10 mL) were heated at reflux overnight. The mixture was evaporated, the residue diluted with ethyl acetate, washed with water and brine, dried (MgSO4) and evaporated. The residue was purified by Biotage flash column chromatography (gradient to 10% ethyl acetate/hexanes) to give product as an oil (1.09 g, quant.); MS for C11H13FNO m/z 322 (M+H)+.

Workup

  1. temperatureat reflux overnight
  2. customThe mixture was evaporated
  3. additionthe residue diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by Biotage flash column chromatography (gradient to 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-c7a30c8a63e44f7fb244951c62ad2a0c
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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