Iodine → 6-Chloro-2-iodo-3-hydroxypyridine

HRID 1776942Notes

Reaction equation

HRID 1776942 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[I:15]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>O>[Cl:1][C:2]1[N:7]=[C:6]([I:15])[C:5]([OH:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 807IodineHCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 8198212-Chloro-5-hydroxypyridine

Product 1

HCID 234331586-Chloro-2-iodo-3-hydroxypyridineYield 71%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-chloropyridin-3-ol (5.0 g, 38.6 mmol) was dissolved in water (50 mL) and placed under an N2 atmosphere. Na2CO3 (8.2 g, 77.4 mmol) was added followed by iodine (9.8 g, 38.8 mmol). The reaction mixture was stirred at room temperature for 2 hours. The mixture was poured into 1M Na2S2O3 and extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4 and concentrated to provide the product of 6-chloro-2-iodopyridin-3-ol (7.0 g, yield: 70.9%). 1H-NMR (CDCl3, 400 MHz) δ 7.17 (d, J=8.4 Hz, 1H), 7.06 (d, J=8.4 Hz, 1H). MS (M+H)+: 256/258.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b87d26b5d7614d598731528afa92582b
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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