Nitric Acid → Methyl 4-bromo-5-nitrothiophene-2-carboxylate

HRID 2216028Notes

Reaction equation

HRID 2216028 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH3:5][O:6][C:7]([C:9]1[S:10][CH:11]=[C:12]([Br:14])[CH:13]=1)=[O:8]>OS(O)(=O)=O>[CH3:5][O:6][C:7]([C:9]1[S:10][C:11]([N+:1]([O-:4])=[O:2])=[C:12]([Br:14])[CH:13]=1)=[O:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 12752071Methyl 4-bromothiophene-2-carboxylate

Product 1

HCID 13291027Methyl 4-bromo-5-nitrothiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Procedure

The nitrating mixture (HNO3 d=1.42, 2 mL; concentrated H2SO4, 6 mL) was slowly added with stirring, at −5 to −10° C., to 4-Bromothiophene-2-carboxylic acid methyl ester (3 g, 13.57 mmol) dissolved in concentrated H2SO4 (10 mL). After being kept at −5 to −10° C. for 30 min. the mixture was poured over crushed ice. The solid precipitate was separated by filtration and washed with water and dried over P2O5 to give 3.7 g of 4-bromo-5-nitrothiophene-2-carboxylic acid methyl ester as a tan solid, which was used in the next step without further purification.

Workup

  1. additionthe mixture was poured
  2. customover crushed ice
  3. customThe solid precipitate was separated by filtration
  4. washwashed with water
  5. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-8351b585ae6c4341b69b4f3146cb2600
Source dataset
uspto-grants-2006_09
Patent number
US07109354B2

Reaction notes

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