Potassium Carbonate → HCID 86682757, compound

Participants

Reaction Conditions

Reaction Steps

In a reactor under an N2-atmosphere, 10.0 g (25.1 mmol) 1-(4-(bromodifluoro-methyl)-3,5-difluorophenyl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane, 4.5 g (30 mmol) of 3,4,5-trifluorophenol, 3.5 g (25 mmol) of potassium carbonate, 2.6 g (7.5 mmol) of tetrabutylphosphonium bromide, 50 ml of H2O and 5 ml of n-heptane were added, and the mixture was refluxed at 82-85° C. for 10 hours. After being cooled to room temperature, the mixture was added with 100 ml of toluene and 100 ml of water, the organic layer was separated, and then the water layer was subjected to extraction with toluene. The organic layer was collected, washed by an aqueous solution of sodium hydrogen carbonate and water in sequence, dried over anhydrous magnesium sulfate, filtered to remove insoluble substance, and concentrated at a reduced pressure. The residue was purified by a fractionation operation utilizing column chromatography, with a mixed solvent of heptane and ethyl acetate in a volume ratio of 1:4 (ethyl acetate:heptane) as an eluent solvent and silica gel as a filler. The product was further purified by recrystallization using isopropanol/ethyl acetate in a volume ratio of 80/20, so that 5.9 g of 1-(4-(difluoro(3,4,5-trifluorophenoxy)methyl)-3,5-difluorophenyl)-4-propyl-2,6,7-trioxabicyclo[2.2.2]octane was obtained as a white solid.

Provenance & Evidence