Nitric Acid → HCID 22277195, Verbindung

HRID 1064125

Reaktionsgleichung

Reaktionsgleichung von HRID 1064125
OS(O)(=O)=O.[Br:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][C:8]=1[C:16]([OH:18])=[O:17].[N+:19]([O-])([OH:21])=[O:20]>>[Br:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([N+:19]([O-:21])=[O:20])[C:8]=1[C:16]([OH:18])=[O:17]

Komponenten

4

Edukt 3

HCID 944Nitric AcidHCID 1118Sulfuric Acid2×HCID 813614-Bromo-1,3-benzenedicarboxylic acid

Produkt 1

HCID 22277195HCID 22277195, VerbindungAusbeute 87 %

Versuchsvorschrift

To a 3-L 4-neck round-bottomed flask equipped with a mechanical stirrer, thermometer, 250-mL addition funnel and charged with concentrated H2SO4 (577 mL), was added 4-bromoisophthalic acid (75.0 g, 306 mmol). The white suspension was cooled to ice-bath temperature and a nitrating reagent (pre-prepared by the careful addition of H2SO4 (169 mL) to HNO3 (107 mL)) was slowly added while maintaining an internal reaction temperature of less than 15° C. When addition was complete, the ice-bath was removed and the suspension stirred overnight at room temperature. After approximately 14 hours, the flask was placed in an ice-bath and crushed ice was added to quench the excess nitrating reagent while maintaining an internal temperature less than 40° C. The cream-colored suspension was filtered, and the solids were collected by filtration and washed with a small volume of ice-cold water. The solids were dissolved in methanol and the volatile components were evaporated. The resulting solids were dried at 60° C. in a vacuum oven overnight to afford Intermediate 39(a) (79.6 g) in 87% yield.

Aufarbeitung

  1. customTo a 3-L 4-neck round-bottomed flask equipped with a mechanical stirrer
  2. additionthermometer, 250-mL addition funnel
  3. temperatureThe white suspension was cooled to ice-bath temperature
  4. additionwas slowly added
  5. temperaturewhile maintaining an internal reaction temperature of less than 15° C
  6. additionWhen addition
  7. customthe ice-bath was removed
  8. waitAfter approximately 14 hours
  9. customthe flask was placed in an ice-bath
  10. customcrushed ice
  11. additionwas added
  12. customto quench the excess nitrating reagent
  13. temperaturewhile maintaining an internal temperature less than 40° C
  14. filtrationThe cream-colored suspension was filtered
  15. filtrationthe solids were collected by filtration
  16. washwashed with a small volume of ice-cold water
  17. dissolutionThe solids were dissolved in methanol
  18. customthe volatile components were evaporated
  19. customThe resulting solids were dried at 60° C. in a vacuum oven overnight

Quellen und Nachweise

ORD-Eintrag
ord-1661537c9dc84ede89b640a54587d3d1
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06967198B2

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