Water → Methyl 4-(2-cyano-3-ethylphenoxy)-3-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-(2-bromo-3-ethylphenoxy)-3-methylbenzoate (1.0 g, 2.9 mmol) in N,N-dimethylformamide was added tetrakis(triphenylphosphine) palladium(0) (0.35 g, 0.3 mmol) and zinc cyanide (1.2 g, 10 mmol). The reaction mixture was stirred at 140° C. for 12 hours. After the reaction, the mixture was poured into water (50 mL) and the solution was extracted with ethyl acetate (50 mL). The organic phase was dried over anhydrous sodium sulfate. The mixture was filtered and the filtrate was concentrated. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=20:1) to give the pure product methyl 4-(2-cyano-3-ethylphenoxy)-3-methylbenzoate as a colorless oil (0.52 g, 61%). 1H NMR (300 MHz, CDCl3): δ 7.99 (d, J=1.8 Hz, 1H), 7.89 (dd, J=8.4 Hz, J=2.1 Hz, 1H), 7.55 (d, J=8.7 Hz, 1H), 6.95 (d, J=8.4 Hz, 1H), 6.86 (d, J=2.4 Hz, 1H), 6.76 (dd, J=8.4 Hz, J=2.4 Hz, 1H), 3.92 (s, 3H), 2.83 (q, J=7.5 Hz, 2H), 2.26 (s, 3H), 1.27 (t, J=7.5 Hz, 3H).

Provenance & Evidence