Aluminum(III) Chloride → 5-Fluoro-1-indanone

Participants

Reaction Steps

A solution of 3-fluorodihydrocinnamoyl chloride (15.4 g) in carbon disulfide (78 ml) was added dropwise to a cold (-5° C.) mixture of aluminium chloride (13.9 g) in carbon disulfide (300 ml) for 30 minutes. During this time and for 30 minutes the mixture was allowed to warm to room temperature (1 hr), then it was heated to reflux (1 hr) and finally the volatiles were removed by distillation under reduced pressure. The residue was dissolved in methylene chloride (400 ml) and washed successively with 10% aqueous sodium hydroxide and water. After drying (magnesium sulfate) and solvent removal in vacuo, 5-fluoroindanone (2 g) was isolated by recrystallisation from hexane.

Provenance & Evidence