Sodium Carbonate → 5-(4′-Formyl[1,1′-biphenyl]-4-yl)-2-furancarboxaldehyde

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-(4-bromophenyl)-furan-2-carboxaldehyde (5 mmol), and tetrakis(triphenylphosphine) palladium (200 mg) in toluene (10 mL) under a nitrogen atmosphere was added 5 mL of a 2 M aqueous solution of Na2CO3 followed by 4-formylphenylboronic acid (6 mmol) in 5 mL of methanol. The vigorously stirred mixture was warmed to 80 ° C. for 12 h. The solvent was evaporated, the precipitate was partitioned between methylene chloride (200 mL) and 2 M aqueous Na2CO3 (15 mL) containing 3 mL of concentrated ammonia. The organic layer was dried (Na2SO4), and then concentrated to dryness under reduced pressure to afford 1 in 85% yield; mp 173-174 ° C. (SiO2, hexanes/EtOAc, 70:30). 1H NMR (DMSO-d6); δ 7.42 (d, J=3.6 Hz, 1H), 7.70 (d, J=3.6 Hz, 1H), 7.93-8.01 (m, 8H), 9.64 (s, 1H), 10.07 (s, 1H). 13C NMR (DMSO-d6); δ 192.7, 177.9, 157.6, 151.8, 144.6, 139.6, 135.3, 130.2, 128.6, 127.9, 127.3, 125.7, 109.5. MS (ESI) m/e (rel. int.): 276 (M+, 100), 247 (5), 219 (25), 189 (25). Anal. Calc. for C8H12O3: C %, 78.24; H %, 4.37. Found C %, 77.99; H %, 4.44.

Provenance & Evidence