Dimethylformamide → 2-Methoxy-6-(4-methoxyphenyl)-1-napthonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-bromo-2-methoxy-6-(4-methoxyphenyl)naphthalene (0.76 g, 2.21 g), CuCN (0.24 g, 2.66 mmol) and DMF (10 mL) was stirred at 120° C. for 4 hr. The reaction mixture was cooled to room temperature, slurried with ethyl acetate, filtered through silica, and evaporation of the solvent, and purification by silica column chromatography (20% ethyl acetate-hexanes) yielded 0.19 g (30%) of the title compound as a pale yellow solid: mp 182–185° C.; 1H NMR (CDCl3): δ 3.88 (3H, s), 4.09 (3H, s), 7.03 (2H, d, J=8.73 Hz), 7.29 (1H, d, J=9.12 Hz), 7.63 (2H, d, J=8.73 Hz), 7.88 (1H, dd, J=1.98 Hz, J=8.73 Hz), 7.97 (1H, d, J=1.98 Hz), 8.09 (1H, d, J=9.12 Hz), 8.14 (1H, d, J=8.73 Hz).

Provenance & Evidence