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

HRID 655218Notes

Reaction equation

HRID 655218 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 451083546-Bromo-5,7-difluoroquinoline

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-1a35cf78a93446f093396b06b5071da6
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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