Potassium Cyanide → 2-Fluoro-4-methylbenzonitrile

Participants

Reaction Conditions

Reaction Steps

2-Fluoro-4-methylaniline (15 g, 120 mmol, 1 eq) was dissolved in 600 ml 1M HCl at 0° C. and a 120 ml aqueous solution of sodium nitrite (12.4 g, 180 mmol, 1.5 eq) was added dropwise, maintaining the temperature under 5° C. The solution was neutralized with solid NaHCO3 and poured into a 600 ml aqueous solution of 36 g KCN and 23.8 g CuCN at 60° C. The solution was stirred for 30 min and cooled to RT. The product was extracted 3 times with EtOAc and the combined organic layers were washed with brine and dried with sodium sulfate. The solvent was removed and 16 g (98%) of product was obtained.

Provenance & Evidence