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

HRID 625966Notes

Reaction equation

HRID 625966 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-olYield 79.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 2-bromopyridin-3-ol (24.1 g, 139 mmol) in 346 mL water was added potassium carbonate (38.3 g, 277 mmol), then iodine (38.7 g, 152 mmol), and this mixture was stirred at room temperature overnight. After cooling to 0° C., 2 N aqueous hydrochloric acid was added until evolution of gas ceased. Acidification was carefully continued until the pH reached ˜6, causing a precipitate to form. This precipitate was collected by filtration, washed with water and dried in a vacuum desiccator until reaching constant mass to afford 2-bromo-6-iodopyridin-3-ol (33 g, 79% yield). ES-MS (M+H)+=300.

Workup

  1. customto form
  2. filtrationThis precipitate was collected by filtration
  3. washwashed with water
  4. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-0a31cefd4b534d42a896438f809e635b
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Reaction notes

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