Nitric Acid → 1,4-Dibromo-2,5-difluoro-3-nitrobenzene

HRID 1270739Notes

Reaction equation

HRID 1270739 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([Br:9])=[CH:4][C:3]=1[F:10].[N+:11]([O-])([OH:13])=[O:12]>S(=O)(=O)(O)O>[Br:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Br:9])=[C:6]([F:8])[C:7]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 675961,4-Dibromo-2,5-difluorobenzene

Product 1

HCID 184514931,4-Dibromo-2,5-difluoro-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

1,4-Dibromo-2,5-difluorobenzene (100 g, 0.37 mol) is dissolved in concentrated sulfuric acid (200 g) and treated with fuming nitric acid (56 g, 0.44 mol, HNO3 content >90%) by drop-wise addition at an internal temperature that is maintained between 50–60° C. After the addition is complete, the mixture is cooled to room temperature and stirred for 12 hours, then poured into ice-water (1000 mL). The suspension is extracted with EtOAc (3×500 mL). The combined organic extracts are dried (MgSO4) and concentrated by rotary evaporator to give 2,5-dibromo-3,6-difluoronitrobenzene as an oily yellow solid.

Workup

  1. temperatureis maintained between 50–60° C
  2. additionAfter the addition
  3. extractionThe suspension is extracted with EtOAc (3×500 mL)
  4. dry with materialThe combined organic extracts are dried (MgSO4)
  5. concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record
ord-3e6a3d40b7e04fbabc412900fdd6f677
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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