Pyridine → 2-(4-Vinylphenoxy)isoindoline-1,3-dione

HRID 587731Notes

Reaction equation

HRID 587731 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)=[CH2:2].[OH:12][N:13]1[C:21](=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]1=[O:23].N1C=CC=CC=1>ClCCCl.O.Cl[Cu]>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([O:12][N:13]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]2=[O:23])=[CH:5][CH:4]=1)=[CH2:2]

Participants

7

Reactant 3

HCID 1049PyridineHCID 10665N-HydroxyphthalimideHCID 27343934-Vinylphenylboronic acid

Product 1

HCID 866751942-(4-Vinylphenoxy)isoindoline-1,3-dioneYield 63%

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a stirred solution of 4-vinylphenylboronic acid (2 g, 13 mmol), 2-hydroxyisoindoline-1,3-dione (3.63 g, 24.53 mmol), and CuCl (1.214 g 12.26 mmol) in 1,2-dichloroethane (50 mL) was added pyridine (1.065 g, 13.48 mmol), and the resultant reaction mixture was stirred at ambient temperature for 48 h. The reaction mixture was diluted with water and extracted with CHCl3. The combined CHCl3 layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash column chromatography (SiO2; 20% EtOAc in petroleum ether) afforded the title compound as a white solid (2 g, 63%): mp 129-131° C.; 1H NMR (400 MHz, CDCl3) δ 7.93 (d, J=2.0 Hz, 2H), 7.82 (d, J=3.2 Hz, 2H), 7.38 (d, J=2.0 Hz, 2H), 7.14 (d, J=2.0 Hz, 2H), 6.70 (m, 1H), 5.83 (d, J=16.0 Hz, 1H), 5.22 (d, J=10.8 Hz, 1H); ESIMS m/z 266.12 ([M+H]+).

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. customPurification by flash column chromatography (SiO2; 20% EtOAc in petroleum ether)

Sources & evidence

ORD record
ord-46717a9cce9a4b22a2adfe210f82a459
Source dataset
uspto-grants-2016_01
Patent number
US09226501B2

Reaction notes

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