Nitric Acid → 3-bromo-2-nitrothiophene

HRID 1370191Notes

Reaction equation

HRID 1370191 reaction equation
[N+:1]([O-:4])(O)=[O:2].C(OC(=O)C)(=O)C.[Br:12][C:13]1[CH:17]=[CH:16][S:15][CH:14]=1>C(O)(=O)C>[Br:12][C:13]1[CH:17]=[CH:16][S:15][C:14]=1[N+:1]([O-:4])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 133833-Bromothiophene

Product 1

HCID 12014963-bromo-2-nitrothiophene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7.4 ml of fuming nitric acid was slowly added to 92.1 ml of acetic acid under ice-cooling, followed by stirring for 10 minutes, and a solution of 52.1 ml of acetic anhydride containing 25 g of 3-bromothiophene was slowly added in such a manner that the bulk temperature did not exceed 10° C., followed by stirring at 10 ° C. for 2 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 17.4 g of the title compound.

Workup

  1. temperaturecooling
  2. customdid not exceed 10° C.
  3. stirringby stirring at 10 ° C. for 2 hours
  4. additionIce was added to the reaction solution
  5. filtrationthe resulting crystals were collected by filtration
  6. washwashed with water and diethyl ether/n-hexane=1/5 successively

Sources & evidence

ORD record
ord-4f032b09762d403b9ad74e2a78a53d80
Source dataset
uspto-grants-2003_06
Patent number
US06583138B1

Reaction notes

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