3,3-bis(4-fluorophenyl)propanoic Acid → 3-(4'-Fluorophenyl)-6-fluoro-1-indanone

HRID 325862Notes

Reaction equation

HRID 325862 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1>S(Cl)(Cl)=O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([CH:8]2[C:5]3[C:6](=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:10](=[O:12])[CH2:9]2)=[CH:14][CH:15]=1

Participants

3

Reactant 1

HCID 102208743,3-bis(4-fluorophenyl)propanoic Acid

Product 1

HCID 131547203-(4'-Fluorophenyl)-6-fluoro-1-indanoneYield 84.6%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 850 grams of 3,3-bis(4-fluorophenyl)-propanoic acid in 600 milliliters of thionylchloride was refluxed for two hours and then concentrated in vacuo. The crude acid chloride was taken up in 2 liters of carbondisulfide. 850 grams of aluminiumchloride were added while stirring and cooling at a temperature of 10-15 degrees Centigrade. The reaction mixture was stirred overnight at room temperature. The reaction mixture was then poured unto crushed ice, and one liter of concentrated hydrochloric acid was added. The mixture was extracted with methylene chloride, and the organic phase was extracted with water and 1 N sodium hydroxide solution. The organic phase was then dried over anhydrous magnesium sulfate, treated with active carbon and concentrated in vacuo. The residue was taken up in hot diisopropylether, an insoluble oil was separated by decanting, and the isopropylether extract was cooled. The crystals which separated out were sucked off and dried to give 670 grams of 3-(4'-fluorophenyl)-6-fluoro-1-indanone melting at 70-73 degrees Centigrade.

Workup

  1. concentrationconcentrated in vacuo
  2. addition850 grams of aluminiumchloride were added
  3. temperaturecooling at a temperature of 10-15 degrees Centigrade
  4. stirringThe reaction mixture was stirred overnight at room temperature
  5. additionThe reaction mixture was then poured
  6. customunto crushed ice, and one liter of concentrated hydrochloric acid
  7. additionwas added
  8. extractionThe mixture was extracted with methylene chloride
  9. extractionthe organic phase was extracted with water and 1 N sodium hydroxide solution
  10. dry with materialThe organic phase was then dried over anhydrous magnesium sulfate
  11. additiontreated with active carbon
  12. concentrationconcentrated in vacuo
  13. customan insoluble oil was separated
  14. customby decanting
  15. extractionthe isopropylether extract
  16. temperaturewas cooled
  17. customThe crystals which separated out
  18. customdried

Sources & evidence

ORD record
ord-80771764051740c7abd71b8ff5e599b6
Source dataset
uspto-grants-1984_04
Patent number
US04443448

Reaction notes

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