Furan-3-boronic acid → HCID 11484311, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-bromo-5H-dibenzo[c,g]chromene-3,9-diol (342 mg, 1.0 mmol), furan-3-boronic acid (224 mg, 2 mmols) and tetrakis(triphenylphosphine)palladium(0) (116 mg, 0.1 mmoles) in DMF (20 ml) is heated at 120° C. with stirring for 4 h. The mixture was filtered through celite, extracted with ethyl acetate (×3), washed with brine, dried over sodium sulfate, filtered, stripped of solvent and purified by silica column chromatography (18%–25% ethyl acetate-hexane) to yield 200 mg (61%) of the title compound as a yellowish solid: mp 216–218° C.; 1H NMR (DMSO-d6): δ 5.00 (2H, s), 6.66 (2H, m), 6.84 (1H, dd, J=8.45 Hz, J=2.35 Hz), 6.93 (1H, dd, J=8.77 Hz, J=2.35 Hz), 7.04 (1H, d, J=2.17 Hz), 7.76 (1H, d, J=8.83 Hz), 7.80–7.85 (3H, m), 8.16 (1H, s), 9.61 (1H, s), 9.71 (1H, s); MS (ESI) m/z 329 (M−H)−, 331(M+H)+.

Provenance & Evidence