Ethyl Acetate → Diethyl (4-amino-3-fluorophenyl)propanedioate

Participants

Reaction Steps

A mixture of diethyl chloro(3-fluoro-4-nitrophenyl)propanedioate and diethyl (3-fluoro-4-nitrophenyl)propanedioate (1.7 g, ˜5.7 mmol) suspended in ethanol was treated with 5-10 ml ethyl acetate until in solution. This was treated with 10% Pd/C (wet paste) (170 mg) under argon and then ammonium formate (1.8 g, 5 eq) added. Stirred for 1 hour at reflux under argon. Cooled to room temperature and Pd removed by filtration through celite, under argon. Evaporated to a brown oil ˜1.7 g. Purified by flash chromatography, 40+™M Si cartridge, eluting 5-40% ethyl acetate in hexane over 10 column volumes. Fraction evaporated to give the title compound as a yellow oil (722 mg).

Provenance & Evidence