Sulfuric Acid → 6-Bromo-5,7-difluoroquinoline

HRID 655218

Reaktionsgleichung

Reaktionsgleichung von HRID 655218
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([NH2:9])=[CH:4][C:3]=1[F:10].[N+]([C:14]1[CH:19]=CC=C[CH:15]=1)([O-])=O.S(=O)(=O)(O)O>OCC(CO)O>[Br:1][C:2]1[C:7]([F:8])=[C:6]2[C:5](=[CH:4][C:3]=1[F:10])[N:9]=[CH:19][CH:14]=[CH:15]2

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 7416NitrobenzeneHCID 27362604-Bromo-3,5-difluoroaniline

Produkt 1

HCID 451083546-Bromo-5,7-difluoroquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 753GlycerolLösungsmittel

Versuchsvorschrift

A mixture of 4-bromo-3,5-difluoro-phenylamine (6.0 g, 28.8 mmole), ferrous sulfate (1.82 g), glycerol (8.6 mL), nitrobenzene (1.79 mL) and 5.0 ml of concentrated sulfuric acid (5 mL) was heated gently. After the first vigorous reaction, the mixture was heated to reflux for five hours. Nitrobenzene was removed by distillation in vacuo. The aqueous solution was acidified with glacial acetic acid, and dark brown precipitate separated, which was purified by flash chromatography (silica gel, petroleum/ethyl acetate=12/1) to return the title compound as a white solid (3.5 g, 49.8%).

Aufarbeitung

  1. temperaturewas heated gently
  2. customAfter the first vigorous reaction
  3. temperaturethe mixture was heated
  4. temperatureto reflux for five hours
  5. customNitrobenzene was removed by distillation in vacuo
  6. customseparated
  7. customwhich was purified by flash chromatography (silica gel, petroleum/ethyl acetate=12/1)

Quellen und Nachweise

ORD-Eintrag
ord-1a35cf78a93446f093396b06b5071da6
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071581B2

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