tert-Butanol → 2-(2-chloro-4-fluorobenzyl)-3-oxopentanoic Acid Methyl Ester

Participants

Reaction Steps

A suspension of potassium tert-butoxide (1.6 g) in anhydrous tetrahydrofuran (25 mL) at 0° C. was treated with a mixture of tert-butanol (1.0 mL) and 3-oxopentanoic acid methyl ester (1.5 g). After stirring at 0° C. for 45 minutes a solution of 1-bromomethyl-2-chloro-4-fluorobenzene (2.6 g) in tetrahydrofuran (5.0 mL) was added and the resulting mixture stirred at room temperature for 3 days. The mixture was diluted with water and the tetrahydrofuran removed under reduced pressure. The mixture was extracted with ethyl acetate and the combined extracts dried over magnesium sulfate and the solvent removed under reduced pressure to afford the title compound, 3.2 g.

Provenance & Evidence