Sodium Carbonate → 2-Chloro-4'-methyl-1,1'-biphenyl

Participants

Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) (637 mg, 0.551 mmol), Na2CO3 (5 mL, 1M) and 4-methylbenzene boronic acid (1.5 g, 11.0 mmol) were added to a solution of 2-chloroiodobenzene (1.315 g, 5.514 mmol) in toluene (98 mL) and EtOH (20 mL). The reaction mixture was heated at reflux for 3 h. The cooled solution was diluted with EtOAc, and the organic solution was washed with water (2×) followed by brine (1×). The organic solution was dried over MgSO4, filtered, and concentrated in vacuo. The product was purified by flash chromatography (hexanes to 10% EtOAC/hexanes) to afford 4′-methyl-2-chloro-biphenyl (1.08 g). 1H NMR (CDCl3 400 MHz) δ 7.49–7.21 (m, 8H), 2.39 (s, 3H).

Provenance & Evidence