Reaction Steps
This reaction is carried out in the same manner as the reaction in example 3. The difference is that, the reactants are p-methoxyphenyl chloride (142.8 mg, 1.0 mmol), 1-(4-fluorophenyl)-1-propanone (183.5 mg, 1.2 mmol), palladium acetate (6.7 mg, 0.030 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino)phenyl(dicyclohexyl)phosphine (18.3 mg, 0.045 mmol), t-BuONa (115.6 mg, 1.2 mmol) in 3 mL dry toluene at 110° C. for 18.5 h. 1-(4′-Fluorophenyl)-2-(4′-methoxyphenyl)-1-propanone (206.7 mg) was obtained with a yield of 80% as liquid. 1H NMR (300 MHz, CDCl3) δ 8.01-7.93 (m, 2H, ArH), 7.22-7.15 (m, 2H, ArH), 7.14-6.99 (m, 2H, ArH), 6.87-6.80 (m, 2H, ArH), 4.59 (q, J=7.0 Hz, 1H, CH), 3.74 (s, 3H, OCH3), 1.50 (d, J=7.0 Hz, 3H, CH3); 13C NMR (75 MHz, CDCl3) δ 198.8, 165.3 (d, J=252.7 Hz), 158.5, 133.3, 132.8 (d, J=2.6 Hz), 131.3 (d, J=8.6 Hz), 128.6, 115.4 (d, J=21.2 Hz), 114.4, 55.1, 47.0, 19.4; 19F NMR (282 MHz, CDCl3) δ −105.7; IR (neat) v (cm−1) 3071, 2974, 2932, 2869, 2837, 1682, 1598, 1514, 1505, 1455, 1409, 1372, 1336, 1302, 1247, 1180, 1157, 1114, 1101, 1035, 1006; MS (70 eV, EI) m/z (%): 259 (M++1, 1.10), 258 (M+, 6.27), 135 (100); HRMS calcd for C16H15O2F (M+): 258.1056. Found: 258.1057.
