Sodium Carbonate → 4'-Nitro[1,1'-biphenyl]-3-carbaldehyde

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Reaction Steps

To a sealable flask containing a mixture of 3-bromobenzaldehyde (1.8 mL, 15 mmol) and Na2CO3 (1.6 g, 15 mmol) in anhydrous DMF (20 mL) and water (10 mL), were added 4-nitrophenylboronic acid (2.5 g, 15 mmol) then palladium(II) acetate (0.17 g, 0.75 mmol). Argon was bubbled through the mixture before the flask was sealed and the mixture stirred at room temperature. After 4 days, the reaction mixture was partitioned between ethyl acetate and brine before the entire mixture was filtered through a pad of Celite®. The aqueous and organic layers, of the filtrate, were separated and the aqueous layer was extracted twice more with EtOAc. All of the organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification by silica gel flash chromatography (ISCO CombiFlash Companion system, 120 g, RediSep normal phase silica flash column, eluting with 10-50% EtOAc in hexane) afforded the desired compound (1.7 g, 47%) as an off-white solid. 1H NMR (CDCl3) δ 10.05 (s, 1H), 8.31-8.25 (m, 2H), 8.10-8.06 (m, 1H), 7.93-7.81 (m, 2H), 7.77-7.70 (m, 2H), 7.63 (t, J=7.7 Hz, 1H). MS (ESI): 228.1 (M+H)+.

Provenance & Evidence