Triacetoxyperiodinane → 1-(2-Bromopyridin-4-yl)ethan-1-one

Participants

Reaction Steps

To a chilled (ice water bath) solution of 1-(2-bromopyridin-4-yl)-ethanol (27.5 g, 132 mmol) in dichloromethane (200 mL) is added Dess-Martin periodinane (56.0 g, 132 mmol). The cold bath is then removed and the mixture is stirred at room temperature. After 2 hours, the mixture is diluted with saturated sodium carbonate (100 mL) and partially concentrated to remove the dichloromethane. The crude material is filtered through filter agent and washed with EtOAc (200 mL). The aqueous layer is separated and extracted with EtOAc (100 mL). The combined organic layers are washed with saturated aqueous sodium carbonate (100 mL), brine (100 mL), dried over magnesium sulfate, filtered and concentrated. The crude material is purified by silica gel chromatography eluting with a gradient of 5-30% EtOAc in hexanes to afford 1-(2-bromopyridin-4-yl)-ethanone as needles.

Provenance & Evidence