Sodium Carbonate → 2-(4-bromophenyl)benzonitrile

Participants

Reaction Steps

Combine 2-iodobenzonitrile (9.0 g, 38.5 mmol), 4-bromophenylboronic acid (10.4 g, 51.8 mmol), 2M aqueous sodium carbonate (20 mL) and tetrakis(triphenylphosphine)-palladium(0) (4.5 g, 3.9 mmol) in 300 mL of dioxane and heat to 80° C. under nitrogen with stirring. After 3 hours cool to room temperature and dilute with 900 mL of ethyl acetate. Wash with water (2×50 mL), brine (1×50 mL) and dry over sodium sulfate. Filter and evaporate to a yellow solid. Chromatograph on silica gel two times, eluting with a gradient of 100% toluene to 1/9 ethyl acetate/toluene to give the title compound as a tan solid, 5.42 g (55%). MS (FAB)=257 (M+); HPLC analysis is 95%.

Provenance & Evidence