N-Hydroxyphthalimide → HCID 14621666, compound

HRID 653850Notes

Reaction equation

HRID 653850 reaction equation
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].Br[CH2:14][F:15].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[F:15][CH2:14][O:1][N:2]1[C:3](=[O:12])[C:4]2=[CH:11][CH:10]=[CH:9][CH:8]=[C:5]2[C:6]1=[O:7]

Participants

5

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 11430Potassium CarbonateHCID 61108Bromofluoromethane

Product 1

HCID 14621666HCID 14621666, compoundYield 57.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

N-hydroxyphthalimide (80 g) and bromofluoromethane (63.2 g) were added to dry dimethyl sulfoxide (350 ml) which had been cooled to 0° C. Potassium carbonate (135 g) was added further, followed by stirring at room temperature for 4 hours. Thereafter, nitrogen gas was introduced for 1 hour. The reaction mixture was added to ice water (800 ml), followed by extraction three times with ethyl acetate (500 ml). After washing the extract with saturated saline, anhydrous magnesium sulfate was added to the extract to dry the same. The solvent was distilled off under reduced pressure. Deposited crystals were washed with isopropyl ether and petroleum ether to obtain the target product (55 g).

Workup

  1. additionThereafter, nitrogen gas was introduced for 1 hour
  2. extractionfollowed by extraction three times with ethyl acetate (500 ml)
  3. washAfter washing the
  4. extractionextract with saturated saline, anhydrous magnesium sulfate
  5. additionwas added to the
  6. extractionextract
  7. customto dry the same
  8. distillationThe solvent was distilled off under reduced pressure
  9. washDeposited crystals were washed with isopropyl ether and petroleum ether

Sources & evidence

ORD record
ord-71ab30362c324417a7868f7587b564b7
Source dataset
uspto-grants-1992_07
Patent number
US05128465

Reaction notes

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