Sulfuric Acid → 6-Bromo-7-fluoroquinoline

HRID 655221Notes

Reaction equation

HRID 655221 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[F:9].[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:7]=[C:6]2[C:5](=[CH:4][C:3]=1[F:9])[N:8]=[CH:18][CH:13]=[CH:14]2

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7416NitrobenzeneHCID 8218484-Bromo-3-fluoroaniline

Product 1

HCID 145483436-Bromo-7-fluoroquinoline

Reagents, catalysts & solvents 1

HCID 753GlycerolSolvent

Procedure

A mixture of 4-bromo-3-fluoro-phenylamine (2.85 g, 15 m mole), ferrous sulfate (0.95 g), glycerol (5.658 g, 4.5 ml), nitrobenzene (1.125 g, 0.93 ml) and concentrated sulfuric acid (2.61 mL) were heated gently. After the first vigorous reaction, the mixture was heated to reflux for 7 hours. Nitrobenzene was evaporated 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=8/1) to return compound title as white crystals (1.44 g, 42.5%).

Workup

  1. temperaturewere heated gently
  2. customAfter the first vigorous reaction
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 7 hours
  5. customNitrobenzene was evaporated in vacuo
  6. customseparated
  7. customwhich was purified by flash chromatography (silica gel, petroleum/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-93d129a240b948e999beb79e75504d8d
Source dataset
uspto-grants-2011_12
Patent number
US08071581B2

Reaction notes

Loading…