Glycerol → 6-Bromo-7-fluoroquinoline

HRID 1890911Notes

Reaction equation

HRID 1890911 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[F:9].O[CH2:11][CH:12]([CH2:14]O)O.[N+](C1C=CC=CC=1)([O-])=O.S(=O)(=O)(O)O>>[Br:1][C:2]1[CH:8]=[C:7]2[C:5](=[CH:4][C:3]=1[F:9])[N:6]=[CH:14][CH:12]=[CH:11]2

Participants

5

Reactant 4

HCID 753GlycerolHCID 1118Sulfuric AcidHCID 7416NitrobenzeneHCID 8218484-Bromo-3-fluoroaniline

Product 1

HCID 145483436-Bromo-7-fluoroquinolineYield 42.5%

Procedure

A mixture of 4-bromo-3-fluoroaniline (2.85 g, 15 mmol), ferric sulfate (0.95 g, 6.25 mmol), glycerol (5.66 g, 61 mmol), nitrobenzene (0.93 mL, 9.1 mmol), and concentrated sulfuric acid (2.61 ml) was heated gently. After the first vigorous reaction, the mixture was boiled for 7 h. Nitrobenzene was then evaporated in vacuo. The aqueous solution was acidified with glacial acetic acid, and a dark brown precipitate separated, which was collected and purified by flash chromatography (silica gel, petroleum/ethyl acetate=8/1) to give 1.44 g of 6-bromo-7-fluoro-quinoline as white crystals (42.5% yield).

Workup

  1. temperaturewas heated gently
  2. customAfter the first vigorous reaction
  3. customNitrobenzene was then evaporated in vacuo
  4. customa dark brown precipitate separated
  5. customwhich was collected
  6. custompurified by flash chromatography (silica gel, petroleum/ethyl acetate=8/1)

Sources & evidence

ORD record
ord-0e4b04955d3c4e08ba1a1ce076b24b01
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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