1-Bromo-4-fluorobenzene → HCID 118105579, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 8-benzyl-3,8-diazabicyclo[3.2.1]octane (2.5 g, 12.36 mmol) in 1,4-dioxane (15 ml) in sealed tube at 25° C. was added 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (0.770 g, 1.23 mmol), sodium tert-butoxide (2.37 g, 24.72 mmol), 1-bromo-4-fluorobenzene (1.63 ml, 14.83 mmol) and tris(dibenzyllideneacetone)dipalladium (0) [Pd2(dba)3] (0.566 g, 0.618 mmol). The resulting reaction mixture was purged with nitrogen for 10 min and stirred at 100° C. for 15 h. The reaction mixture was then cooled to 25° C., filtered through a celite bed, and the celite bed was washed with ethyl acetate (2×20 ml). The combined filtrate was concentrated under reduced pressure to get crude compound. The resulting crude compound was purified by using flash column chromatography over silica gel (100-200 mesh) using 10% ethylacetate in hexane to obtain title compound (2.4 g 66%).

Provenance & Evidence