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

HRID 1359280Notes

Reaction equation

HRID 1359280 reaction equation
CC1C=CC(S(NCl)(=O)=O)=CC=1.[Br:13][C:14]1[C:19]([OH:20])=[CH:18][CH:17]=[CH:16][N:15]=1.[I-:21].[Na+].Cl>C(OCC)(=O)C.O.CN(C)C=O>[Br:13][C:14]1[C:19]([OH:20])=[CH:18][CH:17]=[C:16]([I:21])[N:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5238Sodium IodideHCID 230702-Bromo-3-pyridinolHCID 31388Tosylchloramide

Product 1

HCID 109794792-Bromo-6-iodopyridin-3-olYield 88.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

17.6 g of Chloramine T was added to a mixture of 10.9 g of 2-bromo-3-hydroxypyridine, 9.35 g of sodium iodide and 110 ml of N,N-dimethylformamide under stirring in an ice bath, followed by stirring at the same temperature for 30 minutes and then at room temperature for 10 minutes. Water, ethyl acetate and 11 ml of an aqueous 6N hydrochloric acid solution were added thereto, and the organic phase was washed with brine and the solvent was removed. The residue was subjected to silica gel column chromatography and eluted with 30% ethyl acetate/hexane, to give 16.5 g of the target compound.

Workup

  1. stirringby stirring at the same temperature for 30 minutes
  2. washthe organic phase was washed with brine
  3. customthe solvent was removed
  4. washeluted with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a5488b57bfd148b799793424c0f4dc52
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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