Nitric Acid → 3,4-Dibromo-2-nitrothiophene

HRID 1370192Notes

Reaction equation

HRID 1370192 reaction equation
[N+:1]([O-:4])(O)=[O:2].C(OC(=O)C)(=O)C.[Br:12][C:13]1[C:17]([Br:18])=[CH:16][S:15][CH:14]=1>C(O)(=O)C>[Br:12][C:13]1[C:17]([Br:18])=[CH:16][S:15][C:14]=1[N+:1]([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 184523,4-Dibromothiophene

Product 1

HCID 12015063,4-Dibromo-2-nitrothiophene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

41.4 ml of fuming nitric acid was slowly added to 500 ml of acetic acid under ice-cooling, followed by stirring for 10 minutes, and a solution of 78 ml of acetic acid anhydride containing 50 g of 3,4-dibromothiophene was slowly added, followed by stirring at room temperature for 18 hours. Ice was added to the reaction solution, and the resulting crystals were collected by filtration, and washed with water and diethyl ether/n-hexane=1/5 successively, to give 40.2 g of the title compound.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 18 hours
  3. additionIce was added to the reaction solution
  4. filtrationthe resulting crystals were collected by filtration
  5. washwashed with water and diethyl ether/n-hexane=1/5 successively

Sources & evidence

ORD record
ord-1ad07d63dd9945c993b2f8a62d45aa9c
Source dataset
uspto-grants-2003_06
Patent number
US06583138B1

Reaction notes

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