Dimethylformamide → 2-Fluoro-5-iodo-3-nitropyridine

HRID 1434640Notes

Reaction equation

HRID 1434640 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[F-:12].[K+].CN(C=O)C>[Cl-].[Na+].O>[I:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([F:12])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 522689Potassium FluorideHCID 15142942-Chloro-5-iodo-3-nitropyridine

Product 1

HCID 15142952-Fluoro-5-iodo-3-nitropyridineYield 47.5%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

5-iodo-3-nitro-2-chloropyridine (0.624 g, 2.19 mmol), KF (265 mg, 58.1 mmol), and DMF (3 mL) were stirred at 120 degrees Celsius for 24 h. The mixture was poured into saturated brine, extracted with ethyl acetate, dried over sodium sulfate, then concentrated. The crude residue was purified by flash chromatography using 4-1 hexane:ethyl acetate to yield 5-iodo-3-nitro-2-fluoropyridine (279 mg, 47%) as a colorless solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-56a7e15da4d24f6f83bdcf9ea4135949
Source dataset
uspto-grants-2009_11
Patent number
US07615567B2

Reaction notes

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