Sodium Iodide → 4'-Fluoro-4-iodobutyrophenone

HRID 2362924Notes

Reaction equation

HRID 2362924 reaction equation
[I-:1].[Na+].Cl[CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)=[O:8]>CC(C)=O>[F:15][C:12]1[CH:13]=[CH:14][C:9]([C:7](=[O:8])[CH2:6][CH2:5][CH2:4][I:1])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 197503-(4-Fluorobenzoyl)propyl chloride

Product 1

HCID 30162324'-Fluoro-4-iodobutyrophenoneYield 77.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium iodide (7.47 g, 49.84 mmol, 2 equiv) was added to a solution of 4-chloro-1-(4-fluorophenyl)butan-1-one (5 g, 24.92 mmol, 1 equiv) in acetone. The reaction mixture was refluxed for 16 h. After cooling to ambient temperature, it was evaporated under reduced pressure. The residue was partitioned between ethyl acetate and sodium bisulfite, followed by a wash with brine. The organic layer was dried over MgSO4, filtered and concentrated in vacuo. The crude residue was purified using the Biotage flash chromatography system (SNAP 100 g cartridge, Rf=0.5, gradient—1%-10% ethyl acetate in hexanes) to afford the title compound as a clear oil (5.62 g, 77%). The bottle containing the compound was wrapped in aluminium foil and stored in the freezer to avoid further darkening of the mixture; MS for C10H10FIO m/z 291.98 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. customit was evaporated under reduced pressure
  3. customThe residue was partitioned between ethyl acetate and sodium bisulfite
  4. washa wash with brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified

Sources & evidence

ORD record
ord-76be37765b4f45e98bac436cc24043b3
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

Loading…