1-Phenyl-1-propanone → 2-Fluoro-1-phenylpropan-1-one

HRID 1656804Notes

Reaction equation

HRID 1656804 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:4])[CH2:2][CH3:3].C(NC(C)C)(C)C.[Li].C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:29])(=O)=O)=CC=1>O1CCCC1>[F:29][CH:2]([CH3:3])[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 71481-Phenyl-1-propanoneHCID 588007N-FluorobenzenesulfonimideHCID 45051747Lithium diisopropylamine

Product 1

HCID 894332-Fluoro-1-phenylpropan-1-oneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

1 millimole propiophenone in tetrahydrofuran was dropped into a stirred solution of lithium diisopropylamine in 2 milliliters tetrahydrofuran at -78° C. After 1 hour of stirring, a solution of 1.2 millimoles N-fluorobenzenesulfonimide prepared according to Example 1 above in 3 milliliters tetrahydrofuran was dropped into the reaction mixture and stirring was continued at -78° C. The temperature of the reaction mixture was allowed to rise to 25° C., stirring was continued for 1 hour, and the reaction was quenched by pouring the mixture into saturated ammonium chloride solution. The mixture was neutralized with 1N hydrogen chloride solution and extracted with dichloromethane and the organic phase was washed with water. 2-fluoropropiophenone was obtained in 85% yield.

Workup

  1. additionwas dropped into the reaction mixture
  2. stirringstirring
  3. customwas continued at -78° C
  4. customto rise to 25° C.
  5. stirringstirring
  6. waitwas continued for 1 hour
  7. customthe reaction was quenched
  8. additionby pouring the mixture into saturated ammonium chloride solution
  9. extractionextracted with dichloromethane
  10. washthe organic phase was washed with water

Sources & evidence

ORD record
ord-07387d96cc494c2b9e8131e8162bf686
Source dataset
uspto-grants-1993_10
Patent number
US05254732

Reaction notes

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