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

HRID 723075

Reaction equation

HRID 723075 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-9f2b676568ce42089fc02dfa248c3f0b
Source dataset
uspto-grants-2006_11
Patent number
US07138530B2

Linked notes

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