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18.3.7.2.1.1.4 Variation 4: Reaction of Chloroformates with Sodium Iodide

DOI: 10.1055/sos-SD-118-00276

Aitken, R. A.; Boubalouta, Y.Science of Synthesis Knowledge Updates, (20134136.

It is possible to synthesize various iodoformates 15 from the corresponding chloroformates by halogen exchange using sodium iodide in acetonitrile (Scheme 12).[‌15‌] However, this method requires the use of a low-temperature reactor–extractor to obtain the iodoformates in pentane.[‌16‌] The products are characterized by a dramatic shift in the 13C NMR signal for the carbonyl moiety from 148–151 ppm for the starting chloroformates to 112–116 ppm for the iodoformates.

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