Imidazole → tert-butyl N-(2-iodoethyl)carbamate

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Reaction Steps

To a solution of triphenylphosphine (40 g, 153 mmol) and imidazole (10.4 g, 153 mmol) in CH2Cl2 (375 mL) at RT, is added iodine (40.8 g, 160.6 mmol) portionwise. To this solution is added (2-hydroxyethyl)-carbamic acid tert-butyl ester (24.2 g, 150 mmol) in CH2Cl2 (75 mL) dropwise and the mixture allowed to stir at RT for 14 h. The mixture is then filtered and the filtrate concentrated to a crude red oil, which is partitioned between ether and sat. sodium thiosulfate. The aqueous phase is extracted with ether. The combined organic layers are reduced to 500 mL and then filtered through a plug of silica, eluting with hexane. Evaporation of solvent affords the title compound.

Provenance & Evidence