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

HRID 475239

Reaction equation

HRID 475239 reaction equation
[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]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1235372-Bromo-6-nitrotoluene

Product 1

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

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
5 °C

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-470db701f47c412ab0bb045e48df4d5f
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Linked notes

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