Potassium Carbonate → Methyl 2-(methoxymethyl)-2'-methyl-[1,1'-biphenyl]-4-carboxylate

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Reaction Steps

A mixture of methyl 4-bromo-3-(methoxymethyl)benzoate (40.0 g, 154 mmol), o-tolylboronic acid (23.1 g, 170 mmol), K2CO3 (106.7 g; 772 mmol) and tetrakis(triphenylphosphine)palladium (0) (1.8 g; 1.54 mmol) was prepared in toluene (200 mL) and water (200 mL) and degassed with N2. The reaction mixture was heated at reflux for 1 hour, and then filtered through a pad of Celite and extracted with EtOAc (1 L). The organic layer was washed with a saturated aqueous solution of NaHCO3 (250 mL), water (250 mL) and brine (250 mL), dried (MgSO4) and concentrated affording the title compound as a yellow oil used without further purification (41.9 g, quantitative). HPLC (Method A), Rt 5.3 min (purity: 89.4%).

Provenance & Evidence