Bromine → HCID 18979096, compound

HRID 2393085Notes

Reaction equation

HRID 2393085 reaction equation
[Br:1]Br.[F:3][C:4]1[C:13]([O:14][CH3:15])=[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]([O:14][CH3:15])=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[N:11]2

Participants

4

Reactant 2

HCID 24408BromineHCID 18979058HCID 18979058, compound

Product 1

HCID 18979096HCID 18979096, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

Bromine (0.48 ml) was added dropwise to a solution of 7-fluoro-8-methoxyquinoline (1.6 g) in glacial acetic acid (24 ml). The mixture was heated to 40° C. for 4 h and the reaction quenched with 5% aqueous sodium metabisulphite (100 ml). The solution was basified with 25% aqueous sodium hydroxide to pH13 and the product extracted with ethyl acetate (3×150 ml). The extracts were combined, dried over magnesium sulphate, filtered and the filtrate evaporated in vacuo. The residue was purified by column chromatography on silica gel eluting with 25% ethyl acetate in hexane to yield the desired product as a white solid (0.50 g).

Workup

  1. customthe reaction quenched with 5% aqueous sodium metabisulphite (100 ml)
  2. extractionthe product extracted with ethyl acetate (3×150 ml)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. customthe filtrate evaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel eluting with 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a36ecef352d9474996e2c9470a34074b
Source dataset
uspto-grants-1998_09
Patent number
US05804588

Reaction notes

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