Triacetoxyperiodinane → methyl 2-(4-bromophenyl)-2-oxoacetate

Participants

Reaction Steps

Dess-Martin periodinane (7.6 g, 17.96 mmol) was added to an ambient temperature solution of methyl (4-bromophenyl)(hydroxy)acetate (4 g, 16.33 mmol) in methylene chloride (100 mL). After stirring at ambient temperature for 2 h, the reaction mixture was quenched with saturated aqueous sodium thiosulfate/saturated aqueous sodium bicarbonate (1:1) and extracted with methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Chromatography over silica eluting with 0-50% ethyl acetate/hexane afforded methyl (4-bromophenyl)(oxo)acetate.

Provenance & Evidence