Chloroform → 2-(5-Cyano-2-fluoro-benzoyl)-cyclopropanecarboxylic acid ethyl ester

Participants

Reaction Steps

To a mixture of 2-fluoro-5-cyanophenyl boronic acid (3.10 g,18.8 mmol), 2-p-tolylsulfanylcarbonyl-cyclopropanecarboxylic acid ethyl ester (3.30 g, 12.5 mmol), copper thiophene-2-carboxylate (3.58 g, 18.8 mmol), tris(dibenzylideneacetone)-dipalladium(0).CHCl3 adduct (150 mg, 0.14 mmol), and tri-2-furyl phosphine (0.86 mmol) under N2 was added 125 mL anhydrous THF. The reaction was stirred for 4 h, then poured into 500 mL water and extracted with 500 mL Et2O. The organic layer was extracted with 0.1 N HCl, water, saturated NaHCO3, and water. The organic extract was dried over sodium sulfate, concentrated, and purified by flash chromatography on silica gel using ethyl acetate/hexane (0-10%) as the eluent to yield 2-(5-cyano-2-fluoro-benzoyl)-cyclopropanecarboxylic acid ethyl ester (2.17 g, 66%). 1H NMR (500 MHz, CDCl3) 8.09 (1H, dd, J=2.14, 6.41 Hz), 7.83 (1H, m), 7.31(1H, dd, J=8.55, 10.07 Hz), 4.18 (2H, q, J=7.02 Hz), 3.10 (1H, m), 2.42 (1H, m), 1.68 (2H, m), 1.28 (3H, t, J=7.02 Hz). Anal. calcd. for C14H12FNO3: C, 64.36; H, 4.63; N, 5.36. Found: C, 64.62; H, 4.53; N, 5.26.

Provenance & Evidence