Iodine → HCID 12733231, compound

HRID 261470Notes

Reaction equation

HRID 261470 reaction equation
II.[F:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6]Cl.[Mg].[CH2:13]([N:20]1[CH2:24][CH2:23][C:22](=[O:25])[CH2:21]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CCOCC>[CH2:13]([N:20]1[CH2:24][CH2:23][C:22]([CH2:6][C:5]2[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=2[F:3])([OH:25])[CH2:21]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 807IodineHCID 9580Benzene, 1-(chloromethyl)-2-fluoro-2×HCID 698901-Benzyl-3-pyrrolidinoneHCID 5462224Magnesium

Product 1

HCID 12733231HCID 12733231, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent4×

Procedure

A crystal of iodine followed by a few mls of a solution of 20.6 g of 2-fluorobenzyl chloride in 100 ml of ether is added to a suspension of 3.4 g of magnesium shavings in 50 ml of ether. Thereafter, the reaction is initiated via a hot air gun before adding dropwise, while maintaining the reaction at reflux, the remaining 2-fluorobenzyl chloride solution. After total addition, the reaction is maintained at reflux with stirring for an additional hour before successively adding 100 ml of ether and adding dropwise, with vigorous stirring, a solution of 25.0 g of N-benzyl-3-pyrrolidinone in 100 ml of ether. After complete addition, the resulting suspension is refluxed for an additional 2 hours, stirred at ambient temperature for 16 more hours, and then filtered. The filter cake is washed well with ether and then hydrolyzed by stirring in an ice-ammonium chloride solution. The aqueous solution is extracted thrice with ether and the combined ether extracts are washed successively with water and a sodium chloride solution and then dried. The solvent is removed and the residue is distilled at 135°-140° C., 0.1 mm pressure, to provide a viscous yellow oil which solidifies upon standing. The solid is recrystallized twice from an ethanol-water mixture to give the product, 1-benzyl-3-(2-fluorobenzyl)-3-pyrrolidinol, mp 75°-77° C.

Workup

  1. additionbefore adding dropwise
  2. temperaturewhile maintaining
  3. customthe reaction
  4. temperatureat reflux
  5. additionAfter total addition
  6. temperaturethe reaction is maintained
  7. temperatureat reflux
  8. additionadding dropwise, with vigorous stirring
  9. additionAfter complete addition
  10. temperaturethe resulting suspension is refluxed for an additional 2 hours
  11. stirringstirred at ambient temperature for 16 more hours
  12. filtrationfiltered
  13. washThe filter cake is washed well with ether
  14. stirringhydrolyzed by stirring in an ice-ammonium chloride solution
  15. extractionThe aqueous solution is extracted thrice with ether
  16. washthe combined ether extracts are washed successively with water
  17. dry with materiala sodium chloride solution and then dried
  18. customThe solvent is removed
  19. distillationthe residue is distilled at 135°-140° C.
  20. custom0.1 mm pressure, to provide a viscous yellow oil which
  21. customThe solid is recrystallized twice from an ethanol-water mixture

Sources & evidence

ORD record
ord-c05ea2d7bddd43bba1b171113d4c018a
Source dataset
uspto-grants-1979_08
Patent number
US04166120

Reaction notes

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