Iodine → 5-Chloro-2-iodopyridin-3-ol

HRID 403242Notes

Reaction equation

HRID 403242 reaction equation
[Cl: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>[Cl:1][C:2]1[CH:3]=[C:4]([OH:8])[C:5]([I:15])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 807IodineHCID 10340Sodium CarbonateHCID 5823053-Hydroxy-5-chloropyridine

Product 1

HCID 227146035-Chloro-2-iodopyridin-3-olYield 95.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

To a solution of 5-chloropyridin-3-ol [CAS no 74115-12-1] (15 g, 116 mmol) in sodium carbonate (1 M in water, 232 ml, 232 mmol) at 23° C. was portionwise added iodine (29.4 g, 116 mmol) and the mixture was stirred for 5 h. Poured onto 1 M hydrochloric acid (300 ml), adjusted pH by additional hydrochloric acid to pH 1, the precipitate was filtered off, washed with water, dissolved in ethyl acetate, the organic layer was dried over Na2SO4. Removal of the solvent in vacuum left the 5-chloro-2-iodopyridin-3-ol (28.33 g, 111 mmol, 95.8% yield) as a light brown solid. MS (ISP): m/z=256.1 [(M+H)+] and 258.2 [(M+2+H)+].

Workup

  1. customat 23° C.
  2. filtrationthe precipitate was filtered off
  3. washwashed with water
  4. dissolutiondissolved in ethyl acetate
  5. dry with materialthe organic layer was dried over Na2SO4
  6. customRemoval of the solvent in vacuum

Sources & evidence

ORD record
ord-850c2a1e83d1484ab4039a28061c3e86
Source dataset
uspto-grants-2014_06
Patent number
US08748418B2

Reaction notes

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