Nitrogen → [1,1'-Biphenyl]-3,5-dicarboxaldehyde

Participants

Reaction Conditions

Reaction Steps

A solution of 5-bromoisophthaldehyde (40.0 g, 187.8 mmol), phenylboronic acid (22.9 g, 187.8) and potassium carbonate (64.8 g, 469.5 mmol) in DME/H2O (5:1 600 mL) was purged with N2 for 5 min. Tetrakispalladium triphenyiphosphine (1.1 g mg, 0.9 mmol) was added and the reaction mixture was heated to 90° C. and stirred for 16 h. The reaction mixture was cooled, filtered through a pad of celite and the solvent evaporated under reduced pressure. Purification by column chromatography (10% EtOAc/hexanes) afforded the desired product (74%, 29.1 g) as a tan solid. 1H NMR (300 MHz, CDCl3) δ ppm 10.18 (s, 2H), 8.37 (d, J 1.2 Hz, 2H), 8.35 (t, J=1.5 Hz, 1H), 7.70-7.66 (m, 2H), 7.55-7.43 (m, 3H).

Provenance & Evidence