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

Participants

Reaction Conditions

Reaction Steps

To a solution of 4.4 g (108.6 mmol, 5.7 ml) of acetonitrile diluted in 50 ml of anhydrous tetrahydrofuran are added dropwise at −78° C. under argon 27.1 ml of a N-butyllithium solution (2.5M in hexane, 67.8 mmol), the reaction mixture is stirred 30 min at −78° C., then 5 g (27.15 mmol) of methyl 2-fluoro-4-methoxybenzoate diluted in 30 ml of tetrahydrofuran are added dropwise at −78° C. to the reaction mixture. This mixture is stirred 2 h at −78° C., then a 1M hydrochloric acid solution is added, and the product is extracted several times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate and concentrated. The solid is triturated in 15 ml of methanol to yield 4.4 g (84%) of 3-(2-fluoro-4-methoxyphenyl)-3-oxopropanenitrile in beige solid form.

Provenance & Evidence