Phenylboronic Acid → 3,5-Diphenyl-4-[(2-methoxyethoxy)methoxy]-benzaldehyde

Participants

Reaction Steps

A mixture of 3,5-diiodo-4-(2-methoxyethoxymethyloxy)-benzaldehyde (19.094 g, 41.327 mmol), Pd(OAc)2(0.185 g, 0.02 mmol), phenylboronic acid (11.429 g, 90.920 mmol) and Ba(OH)2.8H2O (39.114 g, 123.981 mmol) in DME (700 ml) and water (110 ml) was refluxed. After 90 minutes, the reaction mixture was cooled, concentrated to about 400 ml and the residue extracted with EtOAc (1×300 ml, 3×100 ml). The combined organics were washed with saturated NaHCO3 (3×75 ml), water (2×75 ml), brine (2×75 ml), dried over Na2SO4, filtered and the filtrate concentrated in vac and dried. The residue was purified by flash chromatography (hexane, 5% and 12% EtOAc/Hex) to give the product as a light yellow viscous oil (11.645 g, 78%); 1H NMR (400 MHz, DMSO-d6) δ 2.79–2.82 (m, 2H), 2.89–2.92 (m, 2H), 3.02 (s, 3H), 4.42 (s, 2H), 7.42–7.46 (m, 2H), 7.48–7.54 (m, 4H), 7.62–7.66 (m, 4H), 7.91 (s, 2H), 10.07 (s, 1H); IR (film) 3050, 2880, 1690, 1580 cm−1; mass spectrum [EI], m/z 362 M+.

Provenance & Evidence