Pyridine → 6-Fluoro-1,2,3,4-tetrahydronaphthalen-2-one

HRID 352275Notes

Reaction equation

HRID 352275 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.S(Cl)(Cl)=O.N1C=CC=[CH:18][CH:17]=1>ClCCCl>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[CH2:8][C:9](=[O:11])[CH2:18][CH2:17]2

Participants

5

Reactant 3

HCID 1049PyridineHCID 98372-(4-Fluorophenyl)acetic acidHCID 24386Thionyl Chloride

Product 1

HCID 50443856-Fluoro-1,2,3,4-tetrahydronaphthalen-2-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 30 g of 4-fluorophenylacetic acid and 48.9 g of thionyl chloride in 60 ml of 1,2-dichloroethane was added a catalytic quantity of pyridine, and the solution was then refluxed for 5 hours under an atmosphere of nitrogen. Following removal of the 1,2-dichloroethane, the product was added dropwise to an ice cooled suspension of 48.6 g of aluminum chloride in 200 ml of dichloromethane. Following stirring for 30 minutes, ethylene gas was blown into the reaction vessel, and after a further 5 hours of stirring, dilute hydrochloric acid was added, and following separation of the organic layer, the aqueous layer was extracted with toluene. The toluene extract was combined with the organic layer and washed subsequently with water, a saturated aqueous solution of sodium bicarbonate, water, and a saturated aqueous solution of sodium chloride, and was then dried over anhydrous sodium sulfate and the solvent removed by evaporation, and subsequently purified by distillation (75° C., 2 Torr) to obtain 19.4 g of 6-fluoro-3,4-dihydro-2(1H)-naphthalenone.

Workup

  1. temperaturethe solution was then refluxed for 5 hours under an atmosphere of nitrogen
  2. customremoval of the 1,2-dichloroethane
  3. additionthe product was added dropwise to an ice
  4. temperaturecooled
  5. additionsuspension of 48.6 g of aluminum chloride in 200 ml of dichloromethane
  6. stirringafter a further 5 hours of stirring
  7. additiondilute hydrochloric acid was added
  8. customseparation of the organic layer
  9. extractionthe aqueous layer was extracted with toluene
  10. extractionThe toluene extract
  11. washwashed subsequently with water
  12. dry with materiala saturated aqueous solution of sodium bicarbonate, water, and a saturated aqueous solution of sodium chloride, and was then dried over anhydrous sodium sulfate
  13. customthe solvent removed by evaporation
  14. distillationsubsequently purified by distillation (75° C., 2 Torr)

Sources & evidence

ORD record
ord-08118a9ae9dd44c5add636d6be5790f6
Source dataset
uspto-grants-2004_06
Patent number
US06746728B1

Reaction notes

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