Iodine → 2,6-Difluoro-3-iodopyridine

HRID 1846771Notes

Reaction equation

HRID 1846771 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.[Li]CCCC.[I:14]I>C1(C)C=CC=CC=1>[F:1][C:2]1[C:7]([I:14])=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1

Participants

5

Reactant 3

HCID 807IodineHCID 739342,6-DifluoropyridineHCID 178418339Butyllithium

Product 1

HCID 197684332,6-Difluoro-3-iodopyridineYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of 2,6-difluoropyridine (1.15 g, 10 mmol, 10. eqv) in toluene (300 ml) was added n-BuLi (4.8 ml, 12 mmol, 1.2 eqv) at −78° C. under nitrogen and the mixture was stirred at the same temperature for 4 hrs. Iodine (2.53 g, 10 mmol) was added with the temperature still below −70° C. The mixture was allowed to warm up to RT and quenched with 10 ml water. The organic solvent was removed under vacuum and the product was collected by filtration. Chromatography by silica gel (petroleum ether: EtOAc=50:1 to 5:1) to give 2,6-difluoro-3-iodopyridine as solid (1.49 g, 6.1 mmol, 61% yield) ESI-MS (M+1): 242 calc. for C5H2F2IN 241.

Workup

  1. customquenched with 10 ml water
  2. customThe organic solvent was removed under vacuum
  3. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-1e84021ed8d44e8483be59b338773c66
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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