Tetrahydrofuran → 4-Methyl-3-(5-(trifluoromethyl)pyridin-2-yloxy)phenylboronic acid

Participants

Reaction Conditions

Reaction Steps

2-(5-Bromo-2-methylphenoxy)-5-(trifluoromethyl)pyridine (1 g, 0.003 mol) and triisopropylborate (0.8 mL, 0.003 mol) were dissolved in toluene (20 mL) and THF (5 mL) and cooled to −78° C. under a N2 atmosphere. n-BuLi (2.69 mL, 0.003 mol) was added while maintaining the reaction at −70° C. and then the reaction was stirred for 1 h at −40° C. Gradually the temperature was increased to −20-0° C. and then the reaction was quenched with 2N HCl. The reaction mixture was warmed to RT, concentrated and extracted with EtOAc. The organic extract was dried over Na2SO4 and concentrated under reduced pressure to give the title compound (1.13 g). m/z (296.4, 298.3, M− H−).

Provenance & Evidence