Iodine → 6-Bromo-2-iodopyridin-3-OL

HRID 611581Notes

Reaction equation

HRID 611581 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[I:15]I>O>[Br:1][C:2]1[N:3]=[C:4]([I:15])[C:5]([OH:8])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 807Iodine2×HCID 10340Sodium CarbonateHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 195977086-Bromo-2-iodopyridin-3-OL

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 4.125 g sample of 2-bromo-5-hydroxypyridine (from step 28c) and 5.28 g of Na2CO3 were dissolved in 75 mL of water. To this solution was added 6.02 g of I2, and the mixture was stirred until the iodine color disappeared. The reaction mixture was then adjusted to pH 5, and extracted with EtOAc. The extract was dried over MgSO4, and the solvent was removed. The residue was chromatographed on silica gel, eluting with 97:3 CHCl3 :MeOH to give 4.3 g of the title compound: 1H NMR (CDCl3, 300 MHz) δ 7.08-7.11 (d, 1H, J=8.5 Hz), 7.29-7.32 (d, 1H, J=8.5 Hz); MS m/z: 300 (M+H)+, 317 (M+NH4)+.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe extract was dried over MgSO4
  3. customthe solvent was removed
  4. customThe residue was chromatographed on silica gel
  5. washeluting with 97:3 CHCl3

Sources & evidence

ORD record
ord-2611ee06cd9a467aa255297607175a28
Source dataset
uspto-grants-1999_12
Patent number
US06001849

Reaction notes

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