Sodium Carbonate → 4'-Chloro-4-ethyl-3-nitrobiphenyl

Participants

Reaction Conditions

Reaction Steps

To 4-bromo-1-ethyl-2-nitrobenzene (20.0 g, 87 mmol) in 1,2-dimethoxyethane (150 ml) is added, at room temperature, 4-chlorophenylboronic acid (14.98 g, 96 mmol) and tetrakis-(triphenylphosphine)palladium(0) (2.0 g, 1.74 mmol) and nitrogen gas is bubbled through the mixture. After stirring for 10 minutes at 20° C., a solution of sodium carbonate (73.8 g, 0.696 mol) in water (350 ml) is added and mixture is refluxed for 16 hours. The reaction mixture is cooled to room temperature, filtered through diatomaceous earth, washing with ethyl acetate (200 ml). The mixture is poured into a separating funnel and the two phases are separated. The aqueous phase is extracted with ethyl acetate. The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure to give 4′-chloro-4-ethyl-3-nitrobiphenyl (23.84 g) as a brown oil used without further purification in the next step.

Provenance & Evidence