Iodine → 2,6-Difluoro-3-iodopyridine

Participants

Reaction Steps

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.

Provenance & Evidence