Hydrogen Bromide → HCID 67362339, compound

HRID 2091470Notes

Reaction equation

HRID 2091470 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:13]C)[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([I:12])=[CH:7]2.Br.[OH-].[Na+]>>[Br:1][C:2]1[CH:3]=[C:4]([OH:13])[CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([I:12])=[CH:7]2

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 67361836HCID 67361836, compound

Product 1

HCID 67362339HCID 67362339, compound

Procedure

A mixture of 8-bromo-3-iodo-6-methoxyquinoline (0.92 g) and conc HBr (11 ml) is heated at reflux during 3 days until no starting material can be detected. After addition of 2 M aq NaOH to reach pH 5 the mixture is extracted with ethyl acetate, the organic phase washed with brine and dried over anhydrous Na2SO4 Evaporation of the organic phase gives 8-bromo-3-iodo-6-hydroxyquinoline as a crude product which is used as such in the next step. 1H NMR (DMSO-d6) δ ppm: 10.50 (1H, br s); 8.9 (1H, d); 8.73 (1H, d); 7.70 (1H, d); 7.15 (1H, d). (M+1)+: 350/352.

Workup

  1. temperatureis heated
  2. temperatureat reflux during 3 days until no starting material
  3. extractionis extracted with ethyl acetate
  4. washthe organic phase washed with brine
  5. dry with materialdried over anhydrous Na2SO4 Evaporation of the organic phase

Sources & evidence

ORD record
ord-be97e0a65b004185ad6bc3841bc96013
Source dataset
uspto-grants-2013_05
Patent number
US08440595B2

Reaction notes

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