Iodine → 6-Chloro-2-iodo-3-hydroxypyridine

HRID 1190264Notes

Reaction equation

HRID 1190264 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.O.C(=O)([O-])[O-].[Na+].[Na+].[I:16]I>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([I:16])[C:5]([OH:8])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 10340Sodium CarbonateHCID 8198212-Chloro-5-hydroxypyridine

Product 1

HCID 234331586-Chloro-2-iodo-3-hydroxypyridineYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To solution of 6-chloro-pyridin-3-ol (112 g, 868 mmol) in THF (800 mL)/Water (800 mL) was added sodium carbonate (92.0 g, 1.736 mol;) and iodine (244.2 g, 1.04 mol;). The reaction mixture was stirred rt 4 h. The aqueous layer containing product was separated and washed with hexane (400 mL×2). The aqueous layer was neutralized to pH=7 with HCl and then extracted EtOAc (500 mL×4). The combined organic layers were dried over Na2SO4, and filtered. The filtrate was concentrated to the crude product, which was washed with EtOAc to afford 163 g of 6-chloro-2-iodopyridin-3-ol, yield: 75%. 1H NMR (DMSO, 400 MHz): δ11.13 (s, 1H, OH), 7.31 (dd, J=8.4, 12.8 Hz, 2H).

Workup

  1. additionThe aqueous layer containing product
  2. customwas separated
  3. washwashed with hexane (400 mL×2)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated to the crude product, which
  7. washwas washed with EtOAc

Sources & evidence

ORD record
ord-af3e446e3577476cb5e0a78f2e495334
Source dataset
uspto-grants-2014_03
Patent number
US08673952B2

Reaction notes

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