Hydrochloric Acid → 3-(2-Fluoro-4-methoxyphenyl)-3-oxopropanenitrile

Participants

Reaction Steps

To a solution of MeCN (4.35 g, 106.0 mmol) in THF (200 mL) at −78° C. was added n-BuLi, 2.5 M in hexanes (32.5 mL, 79.5 mmol). The resulting solution was stirred for 20 minutes and then a solution of 2-fluoro-4-methoxybenzoyl chloride (5.00 g, 26.5 mmol) in tetrahydrofuran (THF) (50 mL) was added slowly. The reaction mixture was allowed to proceed for 1 hour at −78° C. and then saturated aqueous NH4Cl (250 mL) was added. As the reaction warmed to room temperature, it was acidified with 1 N HCl (250 mL). Then, the resulting mixture was extracted with 1:1 EtOAc:hexanes (500 mL), and the organic extract was washed with brine, dried over MgSO4, and evaporated in vacuo to provide 3.5 g (68% crude yield) of the title compound.

Provenance & Evidence