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

関与物質

反応条件

反応手順

To a solution of methyl 4-bromo-3-(methoxymethyl)benzoate (12.0 g, 46.3 mmol, Intermediate A1 step 2) in toluene (150 mL) and water (35 mL) was added 2-ethyl benzene boronic acid (9.0 g, 60.1 mmol) followed by potassium carbonate (19.0 g, 139 mmol) and Pd(PPh3)4 (2.7 g, 2.3 mmol). The resulting mixture was degassed with N2 for 10 min and heated at 100° C. for 12 hours. The reaction mixture was diluted with EtOAc. The organic layer was washed with a saturated aqueous solution of NaHCO3, water (2×) and brine, and then dried (Na2SO4). The solvents were removed under reduced pressure. The residue was purified by chromatography (silica, pet ether/EtOAc) to afford the title compound as a pale yellow oil (12.0 g, 83%). 1H NMR (CDCl3, 400 MHz) δ 8.25 (1H, s), 8.00 (1H, d), 7.35 (2H, m), 7.25 (2H, m), 7.08 (1H, d), 4.17 (2H, m), 3.94 (3H, s), 3.29 (3H, s), 2.43-2.28 (2H, m), 1.03 (3H, t).

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