Triisopropyl borate → Boronic acid, [3-ethoxy-4-(1-methylethoxy)phenyl]-

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To a solution of 2-ethoxy-4-iodo-1-isopropoxybenzene (2.39 g, 7.8 mmol) in THF (25 mL) at −78° C., n-BuLi (1.6 M in hexanes, 6.83 mL, 1.4 eq) was slowly added. The reaction mixture was stirred at −78° C. for 20 min, followed by addition of triisopropyl borate (4.95 mL, 21.5 mmol). The mixture was stirred at −78° C. for 3.0 h and then warmed up to rt over 1.0 h. It was quenched by addition of 5% citric acid (20 mL), followed by a solution of Na2S2O3. After extraction with EtOAc and drying over Na2SO4, the crude product was purified by chromatography to give 1A (1.2 g, 67% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.41 (d, J=6.15 Hz, 6H) 1.49 (t, J=7.03 Hz, 3H) 4.21 (q, J=7.03 Hz, 2H) 4.64 (m, 1H) 7.02 (d, J=8.35 Hz, 1H) 7.70 (s, 1H) 7.79 (m, 1H).

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