Iodine → 2-Bromo-6-iodopyridin-3-ol

HRID 1028570Notes

Reaction equation

HRID 1028570 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>O>[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([I:15])[N:3]=1

Participants

5

Reactant 3

HCID 807IodineHCID 10340Sodium CarbonateHCID 230702-Bromo-3-pyridinol

Product 1

HCID 109794792-Bromo-6-iodopyridin-3-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2-bromopyridin-3-ol (1.00 g, 5.80 mmol) in water (30 mL) was added Na2CO3 (1.23 g, 11.60 mmol) and I2 (1.53 g, 5.80 mmol). After 1 hour, the reaction was quenched with 1 N HCl (20 mL), extracted with EtOAc (2×100 mL), and washed with aq. NaHSO3 and brine (50 mL each). The organic layer was dried over Na2SO4, filtered and concentrated. Purification of the residue by flash chromatography on silica gel (20 to 40% EtOAc/hexanes) afforded 2-bromo-6-iodopyridin-3-ol. Rf=0.44 (25% EtOAc/hexanes). LCMS=301.9 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.56 (d, J=8.3 Hz, 1H), 6.99 (d, J=8.3 Hz, 1H), 5.65 (s, 1H).

Workup

  1. customthe reaction was quenched with 1 N HCl (20 mL)
  2. extractionextracted with EtOAc (2×100 mL)
  3. washwashed with aq. NaHSO3 and brine (50 mL each)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by flash chromatography on silica gel (20 to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ca3ce88099084c2b89805175099787c0
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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