methyl 2-(4-iodophenyl)cyclopropane-1-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared from and according to the general procedure A dry Schlenk flask was charged with methyl 2-(4-iodophenyl)cyclopropanecarboxylate (1.66 g, 5.49 mmol), Na2[PdCl4] (18 mg, 0.06 mmol), 2-(di-tert-butylphosphino)-1-phenylindole (37 mg, 0.11 mmol), CuI (21 mg, 0.11 mmol), and tetramethylethylenediamine (10 mL). The mixture was evacuated and backfilled with Ar (3×), and heated to 70° C. before addition of trimethylsilylacetylene (1.4 mL, 10.8 mmol) through the septum and the temperature was elevated to 80° C. After consumption of the starting material indicated by HPLC, the reaction mixture was cooled to room temperature, quenched with water and extracted with EtOAc (3×). The combined extracts were washed with brine, dried over MgSO4 and concentrated under vacuum and a fraction of the residue was purified by flash chromatography to give 580 mg (40%) after purification by flash chromatography (SiO2, EtOAc:PE, 1:8): Rt: 14.56 min (HPLC method I). The mixture was evacuated was elevated to 80° C After consumption of the starting material quenched with water extracted with EtOAc (3×) The combined extracts were washed with brine dried over MgSO4 concentrated under vacuum a fraction of the residue was purified by flash chromatography to give 580 mg (40%) after purification by flash chromatography (SiO2, EtOAc:PE, 1:8)