4-Fluorobenzyl chloride → 1-[5-[(4-Fluorophenyl)methyl]-2-furanyl]ethanone

Participants

Reaction Conditions

Reaction Steps

A mixture of 9.2 g (83.4 mmol) of 2-acetylfuran, 20 ml (2.0 eq) of 4-fluorobenzylchloride and 22.8 g (2.0 eq) of zinc chloride were stirred at 25° C. for 20 hours. The stirring gradually became difficult due to the precipitate. The mixture was dissolved in water and extracted with ethylacetate. The organic layer was washed with water and a diluted sodium hydrogencarbonate aqueous solution and dried over sodium sulfate. The solvent was removed under deduced pressure. A fractional distillation under reduced pressure of the residue gave 9.6 g of 2-acetyl-5-(4-fluorobenzyl)furan. Yield: 53%. 2 mmHg/120-125° C.

Provenance & Evidence