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

HRID 604212

Reaction equation

HRID 604212 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[I:15]I.Cl>O.C(OCC)(=O)C>[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([I:15])[N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 10340Sodium CarbonateHCID 230702-Bromo-3-pyridinol

Product 1

HCID 109794792-Bromo-6-iodopyridin-3-olYield 52.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Bromo-pyridin-3-ol (5 g) is dissolved in water (150 ml) and thereto are added sodium carbonate (6.15 g) and iodine (7.65 g) and the mixture is stirred at room temperature for 2 hours. Thereto are added a 1N-hydrochloric acid and ethyl acetate, and the mixture is separated, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1→3:1) to give 2-bromo-6-iodo-pyridin-3-ol (4.52 g). MS (m/z): 300/302 [M+H]+

Workup

  1. customthe mixture is separated
  2. washthe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by silica gel column chromatography (hexane:ethyl acetate=9:1→3:1)

Sources & evidence

ORD record
ord-ec2f6c96db704075b3fce92a5613222d
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Linked notes

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