Nitric Acid → 1,4-Dibromo-2-nitrobenzene

HRID 1169361Notes

Reaction equation

HRID 1169361 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][CH:3]=1.[N+:9]([O-])([OH:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 78041,4-DibromobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 770041,4-Dibromo-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

1,4-Dibromobenzene (25 g) was dissolved in concentrated sulfuric acid (30 ml). Thereto was added dropwise under ice cooling a mixed solution of concentrated sulfuric acid (30 ml)/nitric acid (8.9 ml). After 14 hours at room temperature, the reaction mixture was poured into ice water, was mixed with potassium carbonate and was extracted with ethyl acetate. The extract was washed successively with an aqueous solution of potassium bicarbonate and an aqueous saturated solution of sodium chloride, was dried (anhydrous magnesium sulfate) and was then concentrated. The residue was subjected to purification using silica gel column chromatography (hexane) to obtain 1,4-dibromo-2-nitrobenzene (13.3 g) as light yellow crystals.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe extract was washed successively with an aqueous solution of potassium bicarbonate
  3. dry with materialan aqueous saturated solution of sodium chloride, was dried (anhydrous magnesium sulfate)
  4. concentrationwas then concentrated
  5. customThe residue was subjected to purification

Sources & evidence

ORD record
ord-a4a0f06d7ab5402abaf3abe831cc8e70
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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