Hydrochloric Acid → 5-Bromo-2-iodopyridin-3-ol

HRID 1888745Notes

Reaction equation

HRID 1888745 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[N:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[I:15]I.Cl>O>[Br:1][C:2]1[CH:3]=[C:4]([OH:8])[C:5]([I:15])=[N:6][CH:7]=1

Participants

6

Procedure

To a solution of 5-bromopyridin-3-ol (2.75 g, 15.8 mmol) and sodium carbonate (3.35 g, 31.6 mmol) in water (45 mL) was added iodine (4.01 g, 15.8 mmol), and the mixture was stirred at room temperature for 1 hr. 6N Hydrochloric acid (7 mL) was added thereto, and the mixture was weakly acidified with 1N hydrochloric acid (about 5 mL) (pH 4). The resulting solid was collected, washed with water and dissolved in ethyl acetate. The solution was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the obtained solid was washed with a small amount of acetonitrile to give the title compound (3.57 g, yield 75%).

Workup

  1. customThe resulting solid was collected
  2. washwashed with water
  3. dissolutiondissolved in ethyl acetate
  4. washThe solution was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washthe obtained solid was washed with a small amount of acetonitrile

Sources & evidence

ORD record
ord-c0c7771bd99a497b94dc512b24f98020
Source dataset
uspto-grants-2013_08
Patent number
US08501804B2

Reaction notes

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