Nitric Acid → 1-Bromo-2-methyl-3,4-dinitrobenzene

HRID 475239

Reaktionsgleichung

Reaktionsgleichung von HRID 475239
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH3:11].[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N+:12]([O-:14])=[O:13])=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH3:11]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 1235372-Bromo-6-nitrotoluene

Produkt 1

HCID 158896331-Bromo-2-methyl-3,4-dinitrobenzeneAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To a cold (0° C.) solution of 2-bromo-6-nitrotoluene (43.2 g, 0.2 mol) in con H2SO4 (600 mL) was added HNO3 (37 g, 0.24 mol) in small portions with efficient agitation while maintaining the temperature at 0-10° C. The reaction mixture was allowed to slowly warm to RT with stirring overnight then poured into crushed ice (1600 g). The solid was collected by filtration, thoroughly washed with water and dried in air. The crude material was recrystallised from EtOAc/hexanes to afford 40 g (77%) of 1-bromo-2-methyl-3,4-dinitrobenzene (154) as a pale white solid: MS (ESI) m/z=262 [M+1]+.

Aufarbeitung

  1. temperatureto slowly warm to RT
  2. additionthen poured
  3. filtrationThe solid was collected by filtration
  4. washthoroughly washed with water
  5. customdried in air
  6. customThe crude material was recrystallised from EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-470db701f47c412ab0bb045e48df4d5f
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637537B2

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