A mixture of the carboxamide 1468 (5.5 g, 18.8 mmol) and thionyl chloride (35 mL) was refluxed for 3 h under argon and then concentrated under reduced pressure. The residue was purified by flash chromatography (20% EtOAc in hexane) to give 4.12 g (80%) of 2- iodo-4-nitrobenzonitrile 1469 as cream-colored crystals; mp 154–155.5 C° (EtOAc/ hexane, 1:4).
