Cornforth reagent → 2-Bromoimidazo[5,1-b]thiazole-7-carbaldehyde

Participants

Reaction Steps

A suspension of 2-bromo-7-hydroxymethylimidazo [5,1-b]thiazole (24 mg, 0.10 mmol) in dichloromethane (3.5 ml) was added to a solution of pyridinium dichromate (47 mg, 0.13 mmol) in dichloromethane (1.5 ml), and the mixture was stirred at room temperature for 5 hr. After the completion of the reaction, the reaction solution was diluted with ethyl acetate, 4A molecular sieves were added thereto, and the mixture was stirred at room temperature for 20 min. The procedure consisting of filtering the reaction mixture through Celite, adding ethyl acetate to the residue, stirring the mixture, and filtering the stirred mixture through Celite was repeated a few times. The filtrates were combined, and the solvent was removed by distillation under the reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate:methanol=60:1) to give 2-bromoimidazo[5,1-b]thiazole-7-carbaldehyde (11 mg, 47%) as a white solid.

Provenance & Evidence