Bromomethyl 4-methoxyphenyl ketone → 2-[2-(4-methoxyphenyl)-2-oxoethyl]-1H-isoindole-1,3(2H)-dione

HRID 751631Notes

Reaction equation

HRID 751631 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8]Br)=[CH:5][CH:4]=1.[C:13]1(=[O:23])[NH:17][C:16](=[O:18])[C:15]2=[CH:19][CH:20]=[CH:21][CH:22]=[C:14]12.[K]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([C:7](=[O:10])[CH2:8][N:17]2[C:13](=[O:23])[C:14]3[C:15](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:16]2=[O:18])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 24194345Phthalimide potassium salt

Product 1

HCID 28156582-[2-(4-methoxyphenyl)-2-oxoethyl]-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-methoxyphenacyl bromide (5.78 g, 25.23 mmol) in DMF (20 mL) was added potassium phthalimide (5.00 g, 26.99 mmol) and the reaction stirred at rt for 18 h. The reaction mixture was partitioned between dichloromethane (200 mL) and water (100 mL). The layers were separated and the aqueous layer extracted with dichloromethane (3×50 mL). The combined organics were washed with sodium hydroxide (2M, 50 mL), water (50 mL) and brine (50 mL) and dried (MgSO4). Filtration, then concentration in vacuo gave an off white solid. Trituration with diethyl ether followed by collection by filtration gave the title compound as a white solid. δH (CDCl3): 3.86 (3H, s), 5.15 (2H, s), 7.09 (2H, d), 7.81–8.01 (4H, m), 8.05 (2H, d).

Workup

  1. customThe reaction mixture was partitioned between dichloromethane (200 mL) and water (100 mL)
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with dichloromethane (3×50 mL)
  4. washThe combined organics were washed with sodium hydroxide (2M, 50 mL), water (50 mL) and brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration
  7. concentrationconcentration in vacuo
  8. customgave an off white solid
  9. filtrationTrituration with diethyl ether followed by collection by filtration

Sources & evidence

ORD record
ord-c54a7b75e66b4a26a0df7cf492f441b7
Source dataset
uspto-grants-2008_07
Patent number
US07405210B2

Reaction notes

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