Iodine → 5-(4-Chlorophenyl)-2-iodopyridine

Participants

Reaction Steps

40.5 mL (33 mmol) tert-butylnitrite and 54 g (210 mmol) iodine are added to a solution of 38 g (190 mmol) 5-(4-chloro-phenyl)-pyridin-2-ylamine in 400 mL carbon tetrachloride in a flask protected from light and the mixture is stirred for 72 h at RT. A further 40.5 mL (33 mmol) tert-butylnitrite, 54 g (210 mmol) iodine and 100 mL DCM are added. The reaction solution is stirred for a further 24 h at RT. The solvent is eliminated i.vac. and the residue taken up in 125 mL EtOAc and 50 mL water. The aqueous phase is extracted once with EtOAc. The organic phase is dried over Na2SO4 and stirred for one night over activated charcoal. After filtration the solvent is eliminated i.vac. Further purification is carried out by column chromatography on silica gel (PE/EtOAc 9:1).

Provenance & Evidence