Dimethylformamide → Methyl 4-cyano-2-methoxybenzoate

Participants

Reaction Steps

Triphenylphosphine polymer bound (50 mg; 0.15 mmol; 0.15 eq.), palladium (II) acetate (15.04 mg; 0.07 mmol; 0.07 eq.) and DMF (3 mL) were first mixed, purged with N2 and let stirring at RT for 2 h. The vial was then opened, zinc cyanide (117.43 mg; 1 mmol; 1 eq.) and 4-bromo-2-methoxybenzoate (ALDRICH; 653098-10G; 245.07 mg; 1 mmol; 1 eq.) were added and the resulting mixture was purged once more before heating at 140° C. for 50 min. The reaction mixture was then filtrated through a glass frit and the resin was washed with Et2O (3×10 mL). The combined filtrates were washed with water (3×5 mL), once with NaCl sat. solution (10 mL) and then dried over magnesium sulfate. Evaporation of the solvent gave the title compound as a white powder (157 mg; 82%). 1H NMR (DMSO-d6, 400 MHz) δ 7.76 (d, J=7.9 Hz, 1H), 7.68 (d, J=1.4 Hz, 1H), 7.50 (dd, J=7.9, 1.4 Hz, 1H), 3.88 (s, 3H), 3.82 (s, 3H). LC/MS (Method A): 190.8 (M−H)−; 191.8 (M+H)+. HPLC (Method A), Rt 2.67 min (purity: 94.8%).

Provenance & Evidence