Hydrochloric Acid → HCID 59135094, compound

HRID 1028567Notes

Reaction equation

HRID 1028567 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[F:9].C([O-])([O-])=O.[Na+].[Na+].[I:16]I.Cl>O.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([I:16])[C:5]([OH:8])=[CH:4][C:3]=1[F:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 10340Sodium CarbonateHCID 404247372-Chloro-3-fluoro-5-hydroxypyridine

Product 1

HCID 59135094HCID 59135094, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-chloro-5-fluoropyridin-3-ol (307.8 mg, 2.08 mmol) in water (11 mL) was added Na2CO3 (441 mg, 4.16 mmol) and I2 (549 mg, 2.08 mmol). After 2 hours, the reaction mixture was acidified with 1 N HCl to pH 3, diluted with EtOAc (100 mL), and washed with aq. NaHSO3 and brine (50 mL each). The organic layer was dried over Na2SO4, filtered and concentrated to afford 6-chloro-5-fluoro-2-iodopyridin-3-ol. LCMS=273.9 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 7.11 (d, J=8.5 Hz, 1H), 5.47 (d, J=1.4 Hz, 1H).

Workup

  1. washwashed with aq. NaHSO3 and brine (50 mL each)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a8350357e2da4ec5814c2f5ce3885859
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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