Hexane → (5-Ethyl-2-fluorophenyl)boronic acid

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Reaction Steps

To 84B (550 mg, 2.3 mmol) in THF (10 mL) was added 1.6 M n-butyllithium in hexane (2.2 ml, 3.5 mmol) at −78° C. After stirring for 1 h, trimethylborate (0.52 mL, 4.6 mmol) was introduced at −78° C. The reaction mixture was warmed up to rt overnight. It was then quenched by 1.0 N HCl (10 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated. The crude product was purified by column chromatography to give 255 mg white solid of 84C. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.15-1.27 (m, 3H) 2.61 (q, J=7.76 Hz, 2H) 6.94 (t, J=8.57 Hz, 1H) 7.17-7.27 (m, 2H).

Provenance & Evidence