Potassium Carbonate → Methyl 2,2'-dimethyl-1,1'-biphenyl-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-bromo-3-methylbenzoate (ABCR, 15.0 g, 65 mmol) in toluene (200 mL) and water (200 mL), was added o-tolylboronic acid (10.7 g, 78 mmol) followed by potassium carbonate (45.3 g, 32.7 mmol) and tetrakis(triphenylphosphine)palladium(0) (3.78 g, 3.3 mmol). The mixture was degassed with N2 and refluxed at 120° C. for 6 hours. After the completion of reaction, the reaction mixture was cooled to RT. The organic phase was separated and evaporated under reduced pressure. The crude compound was passed through a silica column using hexane as eluent to get the title compound as a white solid (15 g, 95%). 1H NMR (DMSO-d6, 400 MHz) δ 7.91 (s, 1H), 7.82 (m, 1H), 7.32 (m, 2H), 7.27 (m, 1H), 7.24 (m, 1H), 7.06 (m, 1H), 3.84 (s, 3H), 2.09 (s, 3H), 1.95 (s, 3H). HPLC (Method B), Rt 3.01 min (purity: 98.71%).

Provenance & Evidence