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

HRID 1675958Notes

Reaction equation

HRID 1675958 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.Cl>O>[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([I:15])[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 11430Potassium CarbonateHCID 230702-Bromo-3-pyridinol

Product 1

HCID 109794792-Bromo-6-iodopyridin-3-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-bromo-3-hydroxypyridine (11-1, 28 g, 161 mmol) in water (360 mL) was added K2CO3 (22.24 g, 161 mmol) and I2 (20.42 g, 80 mmol). The system was stirred for 1.5 h at ambient temperature, cooled to 0° C. and then treated with concentrated HCl until solids precipitated from solution (pH˜6.0). The solids were isolated by filtration and dried to give the title compound (11-2) as a brown solid. ESI+MS C5H3BrINO: 299.8 found, 299.9 required.

Workup

  1. temperaturecooled to 0° C.
  2. customprecipitated from solution (pH˜6.0)
  3. customThe solids were isolated by filtration
  4. customdried

Sources & evidence

ORD record
ord-b208283f608740318cf7f7a9615f81f9
Source dataset
uspto-grants-2011_08
Patent number
US08003797B2

Reaction notes

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