Bromoform → HCID 22261621, compound

Participants

Reaction Steps

To a solution of 3-(2,2,2-trifluoroethoxy)toluene (7.34 g, 38.6 mmol) in carbon tetrachloride (100 ml) were added N-bromosuccinimide (7.56 g, 42.5 mmol) and 2,2′-azobis(isobutyronitrile) (633 mg, 3.86 mmol) and the mixture was heated under reflux overnight. The insoluble material was filtered using celite and the filtrate was concentrated to prepare a bromo form. To a solution of ethyl 3-oxo-3-(4-fluorophenyl)propionate (7.3 g, 34.7 mmol) in 1,2-dimethoxyethane (70 ml) was added sodium hydride (60% in oil, 1.39 g, 34.7 mmol) under ice-cooling and the mixture was stirred at room temperature for 30 min. To the reaction solution was dropwise added a solution of the bromo form synthesized above in 1,2-dimethoxyethane (20 ml) and the reaction solution was stirred at room temperature for 1 hr. The reaction solution was poured into water (200 ml) and extracted with ethyl acetate (200 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) and recrystallized from diisopropyl ether-hexane to give ethyl-3-(4-fluorophenyl)-3-oxo-2-((3-(2,2,2-trifluoroethoxy)phenyl)methyl)propionate (4.23 g, 31%).

Provenance & Evidence