Phenylboronic Acid → 6-Phenylnicotinaldehyde

Participants

Reaction Steps

Synthesized using compound 43c (1.20 g, 6.44 mmol) and phenylboronic acid (1.18 g, 9.65 mmol) according to Method C. Crude product was purified by flash chromatography on silica-gel using a mixture of hexane/ethyl acetate (10:1) as eluent. Light yellow solid. Yield: 1.10 g, 94%. 1H NMR (CDCl3, 500 MHz): δH (ppm)=7.44-7.52 ppm (m, 3H), 7.87 (d, J=8.2 Hz, 1H), 8.04-8.08 (m, 2H), 8.20 (dd, J=8.2, 2.2 Hz, 1H), 9.10 (dd, J=2.2, 0.6 Hz, 1H), 10.11 (s, 1H); 13C NMR (CDCl3, 125 MHz): δC (ppm)=120.5, 127.5, 129.0, 129.8, 130.4, 136.5, 138.0, 152.4, 162.2, 190.4; MS (ESI): m/z=184.31 [M+H]+.

Provenance & Evidence