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

HRID 59738

Reaktionsgleichung

Reaktionsgleichung von HRID 59738
[Br:1][C:2]1[S:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][CH:3]=1.[N+:12]([O-])([OH:14])=[O:13]>OS(O)(=O)=O>[Br:1][C:2]1[S:6][C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Komponenten

4

Edukt 2

HCID 944Nitric AcidHCID 605723Ethyl 5-bromothiophene-2-carboxylate

Produkt 1

HCID 18957942Ethyl 5-bromo-4-nitrothiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

To a solution of ethyl 5-bromothiophene-2-carboxylate (1.5 g, 6.38 mmol) in aqueous conc. H2SO4 (6 ml) cooled to 0° C., aqueous 65% HNO3 (2 ml) was added, and the reaction was left to warm to RT and stirred for 1 hour. The mixture was poured into ice-water and extracted with EtOAc (×3); the combined organic layers were dried over sodium sulfate and the solvent was removed affording ethyl 5-bromo-4-nitrothiophene-2-carboxylate (Int. 40) which was used without any additional purification (550 mg, 1.964 mmol).

Aufarbeitung

  1. waitthe reaction was left
  2. extractionextracted with EtOAc (×3)
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-579a58a9a073434b8d6c85cba9929bfe
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440954B2

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