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

HRID 751631Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751631
[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

Komponenten

4

Edukt 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 24194345Phthalimide potassium salt

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c54a7b75e66b4a26a0df7cf492f441b7
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405210B2

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