1-Bromo-4-iodobenzene → 1-(4-Bromophenyl)-4-piperidin-1-ylpiperidine

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TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.162 g, 0.18 mmol) was added to 1,4'-bipiperidine (0.595 g, 3.53 mmol), 1-bromo-4-iodobenzene (1.000 g, 3.53 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.205 g, 0.35 mmol) and sodium 2-methylpropan-2-olate (0.408 g, 4.24 mmol) in toluene (10 mL). The resulting mixture was degassed again and was stirred at 80 °C for 18 hours under nitrogen. The reaction mixture was cooled to room temperature and filtered then the filtrate was diluted with EtOAc (50 mL), and washed sequentially with water (50 mL), water (50 mL), and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 10% MeOH in DCM. Pure fractions were evaporated to dryness to afford 1'-(4-bromophenyl)-1,4'-bipiperidine (0.736 g, 64.4 %) as a pale brown oil.

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