6-Bromopyridine-2-carbaldehyde → (6-Bromopyridin-2-yl)(4-fluorophenyl)methanol

Participants

Reaction Steps

To a chilled (−10° C.) solution of 6-bromopyridine-2-carboxaldehyde (5.0 g, 27 mmol) in THF (108 mL) is added a 1 M solution of 4-fluorophenylmagnesium bromide in THF (30 mL, 30 mmol). The temperature is allowed to slowly warm to room temperature over 30 minutes and then the reaction mixture is quenched with saturated aqueous NH4Cl (100 mL) and extracted with EtOAc (3×100 mL). The combined organic layers are dried over Na2SO4 and concentrated. The crude material is purified by silica gel chromatography eluting with 15% EtOAc-hexanes to afford (6-bromopyridin-2-yl)-(4-fluorophenyl)-methanol.

Provenance & Evidence