Boron tribromide → 2-Hydroxy-5-(pyridin-4-yl)benzaldehyde

Participants

Reaction Steps

A solution of aldehyde 192 (700 mg, 3.29 mmol) in DCM (8 mL) at −78° C. is treated with boron tribromide (0.93 mL, 9.85 mmol) dropwise over 5 minutes. After 1 h at −78° C., the reaction is warmed to RT and stirred 2 h. The reaction mixture is then cooled (0° C.), quenched with water (5 mL), basified with aqueous NaHCO3 (10 mL) and extracted into DCM (3×20 mL). The combined organic phases are dried over Na2SO4 and the solvent removed in vacuo to give the title compound.

Provenance & Evidence