2-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[d]oxazole

3164-13-4

73183-34-3

439090-73-0

2-(4-Bromophenyl)benzo[d]oxazole (5 g, 18.2 mmol), pinacol ester of bisboronic acid (5.1 g, 20.1 mmol) and potassium acetate (5.4 g, 54.7 mmol) were dissolved in 1,4-dioxane (182 ml) and stirred to mix. Subsequently, Pd(dppf)Cl2 (260 mg, 0.36 mmol) was added, and the reaction mixture was heated to 100 °C and stirred for 8 hours. After completion of the reaction, the reaction solution was cooled to room temperature. Water (100 ml) was added to the reaction solution and stirred for 10 min before extraction with tetrahydrofuran (THF). The organic layer was separated and the aqueous layer was discarded. The organic layer was dried with anhydrous magnesium sulfate (MgSO4) and subsequently concentrated. The concentrate was recrystallized with ethanol (150 ml) and filtered to give the target compound 2-(4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[d]oxazole (5.3 g, 90% yield). Mass spectrometry result: [M + H] = 322.