6-Bromopyridine-2-carbaldehyde → 1-(6-Bromopyridin-2-yl)prop-2-yn-1-ol

Participants

Reaction Conditions

Reaction Steps

6-Bromo-2-pyridine carboxaldehyde (3.00 g, 16.13 mmol) was dissolved in THF (50 mL) and cooled to −78° C. Ethynylmagnesium bromide (0.5 M in THF, 45.2 mL, 22.58 mmol) was added, and the reaction was allowed to warm to room temperature over 2 h. It was then quenched with saturated NH4Cl and extracted with EtOAc (2×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography (50% EtOAc/hexanes) afforded the title compound as a yellow solid.

Provenance & Evidence