Potassium Iodide → 1-(2-(Benzyloxy)-4-fluorophenyl)ethanone

HRID 1761490Notes

Reaction equation

HRID 1761490 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([OH:11])[CH:3]=1.Cl[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([O:11][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 27373264'-Fluoro-2'-hydroxyacetophenone

Product 1

HCID 212415771-(2-(Benzyloxy)-4-fluorophenyl)ethanoneYield 58%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3 parts of 1-(4-fluoro-2-hydroxyphenyl)ethanone, 14.9 parts of (chloromethyl)benzene, 16.4 parts of potassium carbonate, 0.1 parts of potassium iodide and 120 parts of 2-propanone was stirred overnight at reflux temperature. The reaction mixture was evaporated. The reaction mixture was poured into water. The product was extracted three times with trichloromethane. The combined extracts were dried, filtered and evaporated. The residue was crystallized from a mixture of 2-propanol and water. The product was filtered off and dried, yielding 11 parts (58%) of 1-[4-fluoro-2-(phenylmethoxy)phenyl]ethanone (intermediate 76).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. additionThe reaction mixture was poured into water
  4. extractionThe product was extracted three times with trichloromethane
  5. customThe combined extracts were dried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was crystallized from a mixture of 2-propanol and water
  9. filtrationThe product was filtered off
  10. customdried

Sources & evidence

ORD record
ord-0b16ae3f0f704ca88eb377d1c4258f59
Source dataset
uspto-grants-1989_05
Patent number
US04826848

Reaction notes

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