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

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(2-bromo-pyridin-4-yl)-cyclopropanecarbonitrile (1.16 g, 5.20 mmol) in toluene (30 mL) is added DIBAL-H (10.4 mL, 1M in toluene) at −78° C. The mixture is stirred 1 hour at −78° C. and warmed to room temperature. After 1 hour, ethyl acetate (30 mL) is added, followed by 1M aqueous solution of H2SO4 (30 mL). Phases are separated and the aqueous layer is extracted with ethyl acetate (3×50 mL). The combined organic layers are dried over MgSO4, filtered and concentrated to afford crude 1-(2-bromo-pyridin-4-yl)-cyclopropanecarbaldehyde (ES+ m/z 226.48; 228.47), which is used without purification.

Provenance & Evidence