Cesium carbonate → 1-[3-Fluoro-5-(trifluoromethyl)phenyl]pyrrolidin-3-ol

Participants

Reaction Steps

A solution of 1-bromo-3-fluoro-5-(trifluoromethyl)benzene (10.0 g), 3-hydroxypyrrolidine (3.58 g), palladium(II) acetate (461 mg), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (2.56 g) and cesium carbonate (26.7 g) in toluene (222 ml) was stirred under an argon gas atmosphere at 90° C. for 16 hr. After cooling to room temperature, the reaction mixture was filtered through celite, and the celite was washed with ethyl acetate. The filtrate and washing were combined and the solution was washed with water and saturated brine. This was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate 98:2-20:80) to give the title compound (10.65 g, yield quant.) as a brown oil.

Provenance & Evidence