4-Fluoroiodobenzene → 2-[3-(4-fluorophenyl)-2E-propenyl]-1H-isoindole-1,3(2H)-dione

HRID 2107033Notes

Reaction equation

HRID 2107033 reaction equation
[CH2:1]([N:4]1[C:8](=[O:9])[C:7]2=[CH:10][CH:11]=[CH:12][CH:13]=[C:6]2[C:5]1=[O:14])[CH:2]=[CH2:3].[F:15][C:16]1[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=1>C(#N)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:3]/[CH:2]=[CH:1]/[N:4]2[C:8](=[O:9])[C:7]3[C:6](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:5]2=[O:14])=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 96054-FluoroiodobenzeneHCID 224401N-Allylphthalimide

Product 1

HCID 703628262-[3-(4-fluorophenyl)-2E-propenyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

N-Allylphthalimide (13.9 g, 74.3 mmol), 1-fluoro-4-iodobenzene (15.0 g, 67.6 mmol) triethylamine (15.0 g, 148 mmol) and Pd(OAc)2 (152 mg) were heated at 104° in a glass bomb with shaking for 18 h under an inert atmosphere. The reaction mixture was dissolved in hot acetonitrile. The catalyst was removed by filtration and the filtrate cooled to 0°. The precipitated white solid product was filtered off and dried under vacuum. This title material (12.55 g) was used without further purification.

Workup

  1. customThe catalyst was removed by filtration
  2. temperaturethe filtrate cooled to 0°
  3. filtrationThe precipitated white solid product was filtered off
  4. customdried under vacuum
  5. customThis title material (12.55 g) was used without further purification

Sources & evidence

ORD record
ord-11bde428e3254da58a5f06fea1249da0
Source dataset
uspto-grants-1990_06
Patent number
US04933325

Reaction notes

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