Bromine → 5-Bromo-7-fluoro-8-quinolinol

HRID 573973Notes

Reaction equation

HRID 573973 reaction equation
[Br:1]Br.[F:3][C:4]1[C:13]([OH:14])=[C:12]2[C:7]([CH:8]=[CH:9][CH:10]=[N:11]2)=[CH:6][CH:5]=1>C(O)(=O)C>[Br:1][C:6]1[CH:5]=[C:4]([F:3])[C:13]([OH:14])=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2

Participants

4

Reactant 2

HCID 24408BromineHCID 218230207-Fluoroquinolin-8-ol

Product 1

HCID 443611965-Bromo-7-fluoro-8-quinolinolYield 101.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

An rt solution of bromine (2.34 g, 14.7 mmol) in acetic acid (10 mL) was slowly added to a solution of 7-fluoro-8-quinolinol (2.0 g, 12.2 mmol) in acetic acid (30 mL). The brown reaction mixture was stirred at rt for 16 h, after which the mixture was quenched with saturated sodium bisulfite solution. The resulting mixture was extracted with methyl t-butyl ether 3 times. The combined organic phases were washed with saturated NaHCO3 and brine, dried over Na2SO4, and concentrated in vacuo to dryness to give 3.0 g (97.0%) 5-bromo-7-fluoro-8-quinolinol as a green solid.

Workup

  1. customafter which the mixture was quenched with saturated sodium bisulfite solution
  2. extractionThe resulting mixture was extracted with methyl t-butyl ether 3 times
  3. washThe combined organic phases were washed with saturated NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record
ord-c7d3b8f85f9f4d37977c01f0258e0cd0
Source dataset
uspto-grants-2015_05
Patent number
US09034303B2

Reaction notes

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