Acetonitrile → HCID 46865763, compound

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl(2-bromo-4-chlorophenoxy)acetate (Intermediate 1; 350 mg; 1.09 mmol) and 1-fluorophenylacetylene (Aldrich, 135 μL; 1.20 mmol) in degassed, anhydrous CH3CN (2.80 mL) was treated with dichlorobis(triphenylphosphine)palladium(II) (38 mg; 0.05 mmol), copper(I) iodide (10 mg; 0.05 mmol) and triethylamine (0.45 mL; 3.26 mmol). The reaction mixture was heated at 50° C. under stirring for 16 hours. The solvent was evaporated and the residue purified by column chromatography (silica), eluting with cyclohexane containing increasing amounts of EtOAc. The purified ester intermediate was dissolved in DCM (6 mL) and an HCl solution (4 N in dioxane, 2.7 mL) was added. After stirring for 16 hours, the solvents were removed under vacuum and the crude product purified by preparative HPLC. The title compound was obtained as a light brown solid.

Provenance & Evidence