Sodium Carbonate → 2′-Bromo[1,1′-biphenyl]-4-carboxaldehyde

Participants

Reaction Steps

To a solution of 4-formylbenzeneboronic acid (1.19 g, 7.96 mmol) and Na2CO3 (1.68 g, 15.8 mmol) in water (60 mL) was added p-dioxane (60 mL). This mixture was treated sequentially with 2-bromo iodobenzene (2.25 g, 7.95 mmol) and palladium (II) acetate (159 mg, 0.708 mmol) and allowed to stir at ambient temperature for 16 hours. The solvent was evaporated in vacuo. To the residue was added EtOAc (400 mL) and water (300 mL). The aqueous layer was extracted with EtOAc (2×200 mL). The organic extracts were combined, washed with brine (200 mL), 5% aq. Na2S2O3 (200 mL), brinel (200 mL), dried, (Na2SO4) and the solvent evaporated in vacuo to afford the title compound which was used in the next step without further purification.

Provenance & Evidence