Sodium Iodide → HCID 22718286, compound

HRID 1582755Notes

Reaction equation

HRID 1582755 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.Br[CH2:13][CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[C:8]([C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:11][CH2:13][CH2:14][OH:15])(=[O:10])[CH3:9]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 959922-Acetyl-4-fluorophenol

Product 1

HCID 22718286HCID 22718286, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5′-Fluoro-2′-hydroxyacetophenone 5.0 g, 2-bromoethanol 6.08 g, potassium carbonate 13.4 g and sodium iodide 7.28 g were dissolved in N,N-dimethylformamide 108 ml and stirred at 100° C. overnight. The reaction mixture was cooled and then partitioned by adding water and ethyl acetate. The organic layer was washed with water and then with brine, dried over magnesium sulfate anhydride, and evaporated. The residue was purified by silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound 1.66 g, 26% was obtained as a brown oil.

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned
  3. additionby adding water and ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialwith brine, dried over magnesium sulfate anhydride
  6. customevaporated
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate system), whereby the title compound 1.66 g, 26%
  8. customwas obtained as a brown oil

Sources & evidence

ORD record
ord-a1ad96e4bb2c47d0af795f1068d4769d
Source dataset
uspto-grants-2004_05
Patent number
US06737425B1

Reaction notes

Loading…