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

HRID 661102Notes

Reaction equation

HRID 661102 reaction equation
O.C(=O)([O-])[O-].[Na+].[Na+].[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([OH:15])[CH:14]=1.O.[I:17]I.Cl>>[Br:8][C:9]1[CH:14]=[C:13]([OH:15])[C:12]([I:17])=[N:11][CH:10]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 962WaterHCID 5995293-Bromo-5-hydroxypyridineHCID 2735133Sodium Carbonate Monohydrate

Product 1

HCID 226029855-Bromo-2-iodopyridin-3-olYield 99.4%

Procedure

To a mixture of sodium carbonate monohydrate (1.96 mL, 35.5 mmol) and 3-bromo-5-hydroxypyridine (2.06 g, 11.8 mmol) in H2O (0.213 mL, 11.8 mmol) was added iodine crystals (0.640 mL, 12.4 mmol), and the overall mixture was stirred at room temperature overnight. The mixture was then poured slowly into 2M HCl(aq), and the pH was adjusted to ˜3. The product was collected by filtration followed by crystallization from EtOH/water to afford 5-bromo-2-iodopyridin-3-ol as an off-white solid of (3.53 g, 99.4% yield) m/z (%): 301.2 (100%, M++H).

Workup

  1. filtrationThe product was collected by filtration
  2. customfollowed by crystallization from EtOH/water

Sources & evidence

ORD record
ord-1a5407e86b4140a59bfae67480841bd8
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

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