Sulfuric Acid → 6-Bromo-8-fluoroquinoline

HRID 655236Notes

Reaction equation

HRID 655236 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([F:9])[CH:3]=1.[N+]([C:13]1[CH:18]=CC=C[CH:14]=1)([O-])=O.S(=O)(=O)(O)O>OCC(CO)O>[Br:1][C:2]1[CH:8]=[C:7]2[C:5](=[C:4]([F:9])[CH:3]=1)[N:6]=[CH:18][CH:13]=[CH:14]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7416NitrobenzeneHCID 1230504-Bromo-2-fluoroaniline

Product 1

HCID 467388856-Bromo-8-fluoroquinoline

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Procedure

A mixture of 4-bromo-2-fluoroaniline (12.825 g, 67.5 mmol), 4.275 g of ferrous sulfate, 25.46 g (20.2 ml) of glycerol, 5.067 g (4.2 ml) of nitrobenzene and 11.79 ml of concentrated sulfuric acid was heated gently. After the first vigorous reaction, the mixture was boiled for 7 hours. The nitrobenzene was removed in vacuo. Water was added. The aqueous solution was acidified with glacial acetic acid, and the dark brown precipitate separated, which was purified by flash chromatography (silica gel, petroleum/ethyl acetate=12/1) to return the title compound as white solid (9.72 g, 63.7%).

Workup

  1. temperaturewas heated gently
  2. customAfter the first vigorous reaction
  3. customThe nitrobenzene was removed in vacuo
  4. additionWater was added
  5. customthe dark brown precipitate separated
  6. customwhich was purified by flash chromatography (silica gel, petroleum/ethyl acetate=12/1)

Sources & evidence

ORD record
ord-3be619da0723434ba25e0aedad143252
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

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