N-bromobutanimide → 3-Hydroxy-6-nitroisobenzofuran-1(3h)-one

HRID 280841

Reaktionsgleichung

Reaktionsgleichung von HRID 280841
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][O:9][C:10]2=[O:13])=[CH:6][CH:5]=1)([O-:3])=[O:2].BrN1C(=[O:20])CCC1=O>C(Cl)(Cl)(Cl)Cl>[OH:20][CH:8]1[C:7]2[C:11](=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[C:10](=[O:13])[O:9]1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 2235846-Nitrophthalide

Produkt 1

HCID 5226713-Hydroxy-6-nitroisobenzofuran-1(3h)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

A mixture of 6-nitro-1(3H)-isobenzofuranone (8.99 g, 50.0 mmol) and N-bromosuccinimide (8.9 g, 50.0 mmol) in carbon tetrachloride (135 mL) was stirred and heated under reflux for one hour during which time the reaction mixture was exposed to the light from a 275 Watt, 125 Volt Hanovia sunlamp that was situated 8 inches from the flask. After cooling, the succinimide was removed by filtration, and the filtrate was evaporated in vacuo. The oily residue was mixed with water (200 mL), and the mixture was refluxed for one hour to give a clear, colorless solution. On cooling, the Compound 3a crystallized from solution. An analytical sample was prepared by recrystallization from water; m.p. 157°-160° C.; IR 3390 cm-1 (OH), 1770 cm-1 (C=O), 1H NMR (CDCl3 -Me2SO-d6 -D2O) δ6.78 (s, br, 1H, H3), 7.88 (d, 1H, H4, J4,5 =9 Hz), 8.56 (d, 1H, H5, J=9 Hz), 8.62 (s, 1H, H6).

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux for one hour during which time the reaction mixture
  3. temperatureAfter cooling
  4. customthe succinimide was removed by filtration
  5. customthe filtrate was evaporated in vacuo
  6. additionThe oily residue was mixed with water (200 mL)
  7. temperaturethe mixture was refluxed for one hour
  8. customto give a clear, colorless solution
  9. temperatureOn cooling
  10. customthe Compound 3a crystallized from solution
  11. customAn analytical sample was prepared by recrystallization from water

Quellen und Nachweise

ORD-Eintrag
ord-1922f23bade84f599a4681be49eeba44
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04591587

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