Triacetoxyperiodinane → 3-Bromo-4-methylpyridine-2-carbaldehyde

Participants

Reaction Steps

A mixture of (3-bromo-4-methyl-2-pyridyl)methanol (600 mg, 2.97 mmol) and Dess-Martin Periodinane (1688 mg, 3.86 mmol) in DCM (20 mL) was stirred at room temperature for 3 hours. The reaction mixture was diluted with dichloromethane (50 mL) and washed with saturated aqueous sodium bicarbonate (2×25 mL). The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo to provide a residue that was purified by flash chromatography (12 g, Silica, 0-80% ethyl acetate in heptane). Desired fractions were combined and evaporated in vacuo to afford the title compound as pale yellow solid (470 mg, 79%), which was used in the next step without further purification.

Provenance & Evidence