2,4-Difluoroaniline → CPS 49

HRID 2251830Notes

Reaction equation

HRID 2251830 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[F:10][C:11]1[C:12]([F:24])=[C:13]([F:23])[C:14]([F:22])=[C:15]2[C:20](=O)[O:19][C:17](=[O:18])[C:16]=12>C(O)(=O)C>[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[N:4]1[C:17](=[O:18])[C:16]2[C:15](=[C:14]([F:22])[C:13]([F:23])=[C:12]([F:24])[C:11]=2[F:10])[C:20]1=[O:19]

Participants

4

Reactant 2

HCID 97092,4-DifluoroanilineHCID 69545Tetrafluorophthalic anhydride

Product 1

HCID 9905583CPS 49Yield 42.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of about 1 g (about 7.75 mmol) of 2,4-difluoroaniline, about 1.54 g (about 7 mmol) of tetrafluorophthalic anhydride and about 50 mL of glacial acetic acid was refluxed for about 3.5 hours. The solvent was evaporated to dryness under reduced pressure of from about 200 to about 15 mbar. The residue was dissolved in about 75 mL of CH2C12. The solution was washed three times with about 25 mL of about 0.1 M HCl and twice with about 25 mL of water. The residue was then dried with Na2SO4. After removal of the solvent, the residue was recrystallized from ethyl alcohol to yield about 980 mg (about 42%) of 2-(2,4-difluorophenyl)-4,5,6,7-tetrafluoro-1H-isoindole-1,3(2H)-dione with a melting point of about 145° to about 146° C.

Workup

  1. temperaturewas refluxed for about 3.5 hours
  2. customThe solvent was evaporated to dryness under reduced pressure of from about 200 to about 15 mbar
  3. dissolutionThe residue was dissolved in about 75 mL of CH2C12
  4. washThe solution was washed three times with about 25 mL of about 0.1 M HCl
  5. dry with materialThe residue was then dried with Na2SO4
  6. customAfter removal of the solvent
  7. customthe residue was recrystallized from ethyl alcohol

Sources & evidence

ORD record
ord-34b193c940934bfebd3437ce70cc619e
Source dataset
uspto-grants-2008_01
Patent number
US07320991B2

Reaction notes

Loading…