Acetone → 4-(2-oxopropyl)benzonitrile

Participants

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-chlorobenzonitrile (137.6 mg, 1.0 mmol), palladium cinnamyl chloride (7.9 mg, 0.015 mmol), 2-Methoxy-6-(N-methyl-N-phenyl-amino) henyldicyclohexyl)phosphine (24.5 mg, 0.060 mmol), Cs2CO3 (651.9 mg, 2.0 mmol) in 4.0 mL acetone at 90° C. for 12 h. 4-(2′-Oxopropyl)benzonitrile (127.6 mg) was obtained with a yield of 80% as solid. m.p.: 79.8-80.1° C. (n-Hexane:Ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.66-7.60 (m, 2H, ArH), 7.34-7.27 (m, 2H, ArH), 3.81 (s, 2H, CH2), 2.23 (s, 3H, CH3); 13C NMR (75 MHz, CDCl3) δ 204.3, 139.3, 132.3, 130.3, 118.6, 111.0, 50.3, 29.8; IR (KBr) v (cm−1) 3060, 3006, 2954, 2893, 2225, 1708, 1608, 1420, 1504, 1407, 1356, 1334, 1313, 1212, 1163, 1019; MS (70 eV, EI) m/z (%): 160 (M++1, 1.05), 159 (M+, 9.09), 43 (100).

Provenance & Evidence