p-Vinylbenzyl chloride → 2-[(4-Ethenylphenyl)methyl]-1H-isoindole-1,3(2H)-dione

HRID 1504666Notes

Reaction equation

HRID 1504666 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH2:10])=[CH:5][CH:4]=1.[C:11]1(=[O:21])[NH:15][C:14](=[O:16])[C:13]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:12]12.[K]>CN(C=O)C.O>[CH:9]([C:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:15]2[C:11](=[O:21])[C:12]3[C:13](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:14]2=[O:16])=[CH:4][CH:5]=1)=[CH2:10]

Participants

5

Reactant 2

HCID 74126p-Vinylbenzyl chlorideHCID 24194345Phthalimide potassium salt

Product 1

HCID 197666392-[(4-Ethenylphenyl)methyl]-1H-isoindole-1,3(2H)-dioneYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 1-(chloromethyl)-4-vinylbenzene (10 g, 66 mmol) in DMF (100 mL) was added potassium phthalimide (13.3 g, 72.1 mmol), and the resultant reaction mixture was heated at 70° C. for 16 h. The reaction mixture was diluted with H2O and extracted with CHCl3. The combined CHCl3 layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Recrystallization from MeOH afforded the title compound as an off-white solid (8 g, 46%): 1H NMR (400 MHz, CDCl3) δ 7.83 (m, 2H), 7.71 (m, 2H), 7.39 (m, 4H), 6.65 (dd, J=17.6, 10.8 Hz, 1H), 5.72 (d, J=17.6 Hz, 1H), 5.21 (d, J=10.8 Hz, 1H), 4.82 (s, 2H); GCMS m/z 263.2 ([M]+); IR (thin film) 3420, 1133, 718 cm−1.

Workup

  1. customthe resultant reaction mixture
  2. extractionextracted with CHCl3
  3. washThe combined CHCl3 layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customRecrystallization from MeOH

Sources & evidence

ORD record
ord-6c943fc556354926aef2a77f70b16374
Source dataset
uspto-grants-2015_12
Patent number
US09215870B2

Reaction notes

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