Sulfuric Acid → 1-(2-Bromo-4-pyridinyl)cyclopropanecarboxaldehyde

Participants

Reaction Conditions

Reaction Steps

To a chilled (−78° C.) solution of 1-(2-bromopyridin-4-yl)-cyclopropanecarbonitrile (1.16 g, 5.2 mmol) in toluene (30 mL) is added a 1 M solution of diisobutylaluminum hydride (DIBAH) (10.4 mL) in toluene. The mixture stirred at −78° C. for 1 hour and is then warmed to room temperature. After 1 hour, EtOAc (30 mL) is added, followed by 1 M aqueous solution of H2SO4 (30 mL). The organic phase is separated and the aqueous layer is extracted with EtOAc (3×50 mL). The combined organic layers are dried over MgSO4, filtered and concentrated to afford crude 1-(2-bromopyridin-4-yl)-cyclopropanecarboxaldehyde which is used without purification. MS m/z 226.5, 228.5

Provenance & Evidence