Toluene → 4-(4-(4-Methoxyphenyl)thiophen-3-yl)-3-methylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

To a mixture of 3-bromo-4-(4-methoxyphenyl)thiophene (Scheme I, 2, X1=4-methoxyphenyl) (1.7 g, 6.316 mmol), 4-cyano-2-methylphenylboronic acid (Scheme I, 2A, X2=4-cyano-2-methylphenyl) (1.535 g, 6.316 mmol), sodium carbonate (1.34 g, 12.63 mmol), toluene (60 mL) in a mixture of ethanol (36 mL) and water (24 mL) under nitrogen was added Pd(PPh3)4 (0.7 g, 0.606 mmol). The mixture was stirred at 80° C. for 5 h, poured into water (50 mL), and extracted with ethyl acetate (50 mL×3). The organic extracts were dried over anhydrous magnesium sulfate (6 g), evaporated, and purified by column chromatography on silica gel (petroleum ether/ethyl acetate=50:1) to give 4-(4-(4-methoxyphenyl)thiophen-3-yl)-3-methylbenzonitrile (Scheme I, 3, X1=4-methoxyphenyl, X2=4-cyano-2-methylphenyl) (1.34 g, yield 69.4%). 1H NMR (DMSO-d6 400 MHz): δ 7.68-7.65 (m, 3H), 7.58 (d, J=3.2 Hz, 1H), 7.33 (d, J=8.0 Hz, 1H), 6.98 (d, J=8.8 Hz, 2H), 6.80 (d, J=8.8 Hz, 2H), 3.70 (s, 3H), 1.79 (s, 3H).

Provenance & Evidence