1-Bromo-4-fluorobenzene → HCID 89924447, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 1-benzyl-2,2-dimethylpiperazine (1.2 g, 5.87 mmol) in 1,4-dioxane (50 ml) at 25° C. was added 1-bromo-4-fluorobenzene (1.233 g, 7.05 mmol), 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (BINAP) (0.366 g, 0.587 mmol), sodium tert-butoxide (1.129 g, 11.75 mmol), and tris(dibenzyllideneacetone)dipalladium (0) [Pd2(dba)3] (0.269 g, 0.294 mmol). The reaction mixture was purged with nitrogen for 10 min in sealed tube and then heated at 100° C. for 5 h. The progress of reaction was monitored by TLC. The reaction mixture was cooled to 25° C., filtered through celite, washed with ethyl acetate (2×50 ml). The combined filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified over silica gel (100-200 mesh) by flash chromatography using 10% ethyl acetate in hexane as eluent to obtain the title compound (1.1 g, 62.8%)

Provenance & Evidence