Potassium Carbonate → Methyl 2-hydroxy-2'-methyl-[1,1'-biphenyl]-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 4-bromo-3-hydroxybenzoate (Combi-Blocks CA-4189, 25 g, 108 mmol), o-tolylboronic acid (22 g, 162 mmol), anhydrous potassium carbonate (44 g, 324 mmol) and Pd(PPh3)4 (6.25 g, 5.4 mmol) was prepared in a mixture of toluene (500 mL) and water (100 mL), and then degassed with N2. The reaction mixture was heated at 110° C. for 12 hours. The reaction mixture was cooled at RT, filtered through a Celite pad and washed with a 10% aqueous solution of NaHCO3, water and brine. The organic layer was dried (Na2SO4) and concentrated under vacuum. The residue was purified by chromatography (silica, pet ether/EtOAc) to afford of the title compound as a pale yellow solid (20 g, 77%). 1H NMR (DMSO-d6, 400 MHz) δ 9.85 (1H, s), 7.52 (1H, s), 7.45 (1H, d), 7.20-7.25, (3H, m), 7.15 (1H, d), 7.10 (1H, d), 3.84 (3H, s), 2.09 (3H, s).

Provenance & Evidence