5-Fluoro-2-methoxybenzaldehyde → 1-(5-Fluoro-2-methoxy-phenyl)-3-phenyl-prop-2-yn-1-ol

Participants

Reaction Steps

To a stirred solution of 5-fluoro-2-methoxybenzaldehyde (933 mg, 6.05 mmol) in anhydrous THF (15 mL) at 0° C. was added phenylethynyl magnesium bromide solution (1M in THF, 9.0 mL, 9.08 mmol). The temperature was allowed to increase to RT over the course of the reaction. After 18 h, the reaction mixture was quenched with saturated aqueous ammonium chloride solution and extracted with EtOAc (20 mL). The organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 30% EtOAc in cyclohexane) to afford the title compound (1.19 g, 77%). 1H NMR (400 MHz, DMSO-d6): δ 7.42-7.32 (m, 6H), 7.16-7.09 (m, 1H), 7.06-7.02 (m, 1H), 6.16-6.13 (d, 1H), 5.78-5.75 (d, 1H), 3.83 (s, 3H).

Provenance & Evidence