Sodium Iodide → 4-Iodo-1-phenylbutan-1-one

HRID 2363015Notes

Reaction equation

HRID 2363015 reaction equation
[I-:1].[Na+].Cl[CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8]>CC(C)=O>[I:1][CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 2535334-Chlorobutyrophenone

Product 1

HCID 110869514-Iodo-1-phenylbutan-1-oneYield 59%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Sodium iodide (1.64 g, 10.95 mmol, 2 equiv) was added to a solution of 4-chloro-1-phenylbutan-1-one (1 g, 5.475 mmol, 1 equiv) in acetone. The reaction mixture was refluxed for 16 h. After cooling to ambient temperature, it was evaporated under reduced pressure to remove all the acetone. The residue was worked up using 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 falsh chromatography system (SNAP 50 g cartridge, Rf=0.4, 5%-30% ethyl acetate in hexanes) to afford the title compound as white solid (880 mg, 59%). The bottle containing the compound was wrapped in aluminium foil to stored in the freezer to avoid further darkening of the mixture; 1H NMR (400 MHz, DMSO-d6): δ 2.06-2.16 (m, 2H); 3.14 (t, 2H, J=3.2 and 4 Hz); 3.34 (t, 2H, J=6.8 and 7.2 Hz); 7.51-7.55 (m, 2H); 7.62-7.67 (m, 2H); 7.95-7.98 (m, 2H); MS for C10H11IO m/z 274.99 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 h
  2. customit was evaporated under reduced pressure
  3. customto remove all the acetone
  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-c5e353d0d1ae485cad5eede765d89b0e
Source dataset
uspto-grants-2014_04
Patent number
US08691836B2

Reaction notes

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