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

HRID 1693375Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1693375
[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-b1f09a387b7441a8aeeefd13188c333c
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08158622B2

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