Bromine → 4-Bromo-6-isopropyl-2-methyl-5-(pentafluorophenoxy)indan-1-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of 17.5 g (131 mmol) of AlCl3 in 28 ml of dichloromethane cooled to −20° C. a solution of 32.4 g (87.5 mmol) of 6-isopropyl-2-methyl-5-(pentafluorophenoxy)indan-1-one in 46 ml of dichloromethane was added dropwise. Further on, this solution was warmed to 0° C., and 4.80 ml (96.0 mmol) of bromine was added dropwise by vigorous stirring for 0.5 h. This mixture was stirred for 24 h at room temperature and then poured in cold aqueous Na2SO3 to remove an excess of bromine. The product was extracted with 3×50 ml of dichloromethane. The combined extract was evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: n-hexane-dichloromethane-ether 50:50:1, vol.). Yield 20.1 g (51%). Additionally, 15.0 g of the starting indanone was recovered.

Provenance & Evidence