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

HRID 1862482Notes

Reaction equation

HRID 1862482 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-8063fbd2f3ac4951bb5fe737c56393a2
Source dataset
uspto-grants-2003_03
Patent number
US06538010B1

Reaction notes

Loading…