Dimethylformamide → 2-Formyl-5-methoxybenzonitrile

Participants

Reaction Steps

To a stirred solution of 4-cyano-2-fluorobenzaldehyde (0.5 g, 3.4 mmol) in dry dimethylformamide (3 ml) cooled to 5° C. under a nitrogen atmosphere, a solution of freshly prepared sodium methoxide in methanol (1.41M, 2.62 ml) was added slowly, dropwise. After addition, the reaction mixture was stirred at room temperature for 22 hours. A few drops of water were then added and the turbid solution filtered through celite. The filtrate was further diluted with water until crystallisation commenced to give 2-cyano-4-methoxybenzaldeyde as a pale yellow solid. A second crop was recovered from the filtrate.

Provenance & Evidence