Hydrochloric Acid → 2-Bromo-6-iodopyridin-3-ol

HRID 929603Notes

Reaction equation

HRID 929603 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[I:15]I.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].Cl>O>[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([I:15])[N:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 11430Potassium CarbonateHCID 230702-Bromo-3-pyridinolHCID 656671Sodium Pyrosulfite

Product 1

HCID 109794792-Bromo-6-iodopyridin-3-olYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-bromo-3-hydroxypyridine (10 g, 57.5 mmol) and potassium carbonate (15.9 g, 114.9 mmol) in water (130 mL) was added iodine (15 g, 59.2 mmol) and the reaction mixture stirred at room temperature for 23 hours. A small amount of solid sodium metabisulfite was added to the reaction mixture. The reaction mixture was then cooled to 0° C. and acidified to pH 6 by the addition of 1 M aqueous hydrochloric acid. The resulting suspension was stirred at 0° C. for 1 hour then filtered to give 2-bromo-6-iodopyridin-3-ol (13.6 g, 79% yield) as a white solid.

Workup

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. stirringThe resulting suspension was stirred at 0° C. for 1 hour
  3. filtrationthen filtered

Sources & evidence

ORD record
ord-35132641e7dd432ba359d0cbfa6e0e44
Source dataset
uspto-grants-2016_03
Patent number
US09296696B2

Reaction notes

Loading…