Hydrogen Bromide → 4-Bromophthalimide

HRID 562027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 562027
N[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][C:5]2=[O:12].[BrH:13]>S(=O)(=O)(O)O>[Br:13][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[NH:6][C:5]2=[O:12]

Komponenten

4

Edukt 2

HCID 260Hydrogen BromideHCID 729154-Aminophthalimide

Produkt 1

HCID 2360184-BromophthalimideAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 5-amino-1H-isoindole-1,3(2H)-dione (1.0 g, 6.2 mmol) dissolved in sulfuric acid solution (2 mL of Con. H2SO4 in 7.5 mL of H2O) at 0° C., was added ice cold sodium nitrite solution (0.8 g in 2 mL of H2O) dropwise. After 45 min of stirring at 0° C., CuBr (3.4 g, 23.7 mmol) and HBr[48%] (13.6 mL, 4 vol. w.r.t. CuBr) were added at the same temperature. The resulting mixture was stirred at 80° C. for 8 h then poured into crushed ice. Filtered the solid, washed with ice cold water and dried thoroughly to give 0.6 g (43.0%) of 5-bromo-1H-isoindole-1,3(2H)-dione as a brown colour solid.

Aufarbeitung

  1. stirringThe resulting mixture was stirred at 80° C. for 8 h
  2. additionthen poured
  3. custominto crushed ice
  4. filtrationFiltered the solid
  5. washwashed with ice cold water
  6. customdried thoroughly

Quellen und Nachweise

ORD-Eintrag
ord-9f539b5659ab477489cd05c474bb0522
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063071B2

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