Reaction Steps
This reaction is carried out in the same manner as the reaction in example 3. The difference is that, the reactants are 4-fluorophenyl chloride (130.2 mg, 1.0 mmol), 1-(4-methoxyphenyl)-1-propanone (198.4 mg, 1.2 mmol), palladium acetate (11.1 mg, 0.050 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)phenyldicyclohexyl)phosphine (30.8 mg, 0.075 mmol), t-BuONa (115.0 mg, 1.2 mmol) in 3 mL dry toluene at 110° C. for 12 h. 2-(4′-Fluorophenyl)-1-(4′-methoxyphenyl)-1-propanone (252.8 mg, containing 19% of 1-(4-methoxyphenyl)-1-propanone as determined by 1H NMR analysis) was obtained with a yield of 85% as solid. m.p.: 83.3-84.0° C. (n-hexane/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.98-7.89 (m, 2H, ArH), 7.29-7.20 (m, 2H, ArH), 7.00-6.81 (m, 4H, ArH), 4.64 (q, J=6.9 Hz, 1H, CH), 3.76 (s, 3H, OCH3), 1.49 (d, J=6.9 Hz, 3H, CH3); 13C NMR (75 MHz, CDCl3) δ 198.5, 163.1, 159.9, 137.4 (d, J=2.9 Hz), 130.8, 129.0 (d, J=8.6 Hz), 128.9, 115.5 (d, J=21.0 Hz), 113.5, 55.2, 46.3, 19.4; 19F NMR (282 MHz, CDCl3) δ −115.9; IR (KBr) v (cm−1) 3072, 2975, 2934, 2840, 1674, 1600, 1574, 1510, 1456, 1419, 1373, 1338, 1311, 1258, 1225, 1171, 1114, 1030; MS (70 eV, EI) m/z (%): 258 (M+, 0.32), 135 (100); Anal. Calcd. for C16H15FO2: C, 74.40; H, 5.85. Found: C, 74.23; H, 5.82.
