Phenylboronic Acid → 3,5-Bis-phenyl-4-hydroxybenzoic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of phenylboronic acid (4.95 g, 40.57 mmol), Ba(OH)2.H2O (10.48 g, 55.33 mmol), and Pd(OAc)2 (0.414 g, 1.84 mmol) in DME/H2O (110 mL/20 mL) was added 3,5-diiodo-4-hydroxybenzoic acid methyl ester (7.45 g, 18.44 mmol). The mixture was stirred at 85° C. for 3 h and was then cooled and concentrated. The residue was partitioned between ethyl acetate/2N HCl. The organic phase was dried (MgSO4) and concentrated to give a solid which was triturated with diethyl ether/petroleum ether to give 3.51 g (62.5%) of product as a white solid. 1H NMR (DMSO-d6) δ9.27 (s, 1H), 7.27 (s, 2H), 7.25-7.40 (m, 10H), 3.81 (s, 3H).

Provenance & Evidence