Acetic Acid → 4-(2-Acetyl-3-oxobut-1-en-1-yl)-3-fluorobenzonitrile

Participants

Reaction Steps

120 mg (0.805 mmol) of 3-fluoro-4-formylbenzonitrile, 80.6 mg (0.805 mmol) of 2,4-pentanedione, 72.5 mg (1.21 mmol) of acetic acid and 14 mg (0.16 mmol) of piperidine are dissolved in 8 ml of dichloromethane and heated under reflux with an inverse water trap overnight. The mixture shows complete conversion (TLC check, mobile phase: cyclohexane/ethyl acetate 5:1). The mixture is diluted with dichloromethane, washed with water and saturated sodium chloride solution and dried with sodium sulfate. The solvent is removed in a rotary evaporator. 155 mg (83.3% of theory) of 4-(2-acetyl-3-oxobut-1-en-1-yl)-3-fluorobenzonitrile are obtained and are reacted without further purification.

Provenance & Evidence