Sodium Carbonate → 2-Cyano-4'-methylbiphenyl

Participants

Reaction Steps

To a solution of o-bromobenzonitrile (40 g) and 4-methylbenzeneboronic acid (33 g) in DME (2 liters) was added tetrakis (triphenylphosphine) palladium (0) (7.58 g) and then sodium carbonate (1M, 592 ml). The mixture was stirred vigorously and heated at reflux for 18 hours. The solvent was removed in vacuo and the dark residue partitioned between ether (800 ml) and sodium carbonate (1M, 800 ml); the aqueous phase was extracted with ether (3×400 ml). The combined organic phases were dried and concentrated in vacuo to afford an orange oil which was crystallised from System C (1:3) using activated charcoal as a decolourising agent to afford a white solid (33.0 g).

Provenance & Evidence