N-Iodosuccinimide → TERT-BUTYL 2-IODOTHIOPHEN-3-YLCARBAMATE

Participants

Reaction Steps

In a manner analogous to Campaigne, E. and Monroe, P. A. J.A.C.S., 76, 2447-2450 (1954), to a boiling solution of (tert-butoxy)-N-(3-thienyl)carboxamide (21.0 g, 0.1 mol, preparation 5) in methylene chloride (400 mL) is added N-iodosuccinimide (23.7 g, 0.1 mol) in small portions. The heating bath is then set to 65° C. for 20 min. TLC (Hexane/AcOEt 9:1) shows complete consumption of starting material. The reaction is taken to room temperature, the solvent is evaporated and the crude is purified by flash chromatography (Silica gel-Hexane/EtOAc 9:1) to obtain 30.0 g (88%) of title compound as a white solid.

Provenance & Evidence