4-Methyl-2-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-benzonitrile

Chemical Properties

White-Yellow Crystalline Powder

Preparation

In a glove box, a 100 mL schlenk flask, equipped with a magnetic stirring bar, was charged with Pd2(dba)3 (13.8 mg, 0.015 mmol, 3 mol % Pd) and tricyclohexylphosphine (PCy3, 20.2 mg, 0.072 mmol, 7.2 mol %). Dioxane (6 mL) was added and the resulting mixture was stirred for 30 minutes at room temperature. B2Pin2 (280 mg, 1.1 mmol), KOAc (147 mg, 1.5 mmol), and 2-bromo-4-methylbenzonitrile (196 mg, 1 mmol) were added successively. The schlenk flask was brought to a schlenk line. A condenser was attached, and the flask was flushed with nitrogen. The reaction mixture was stirred at 80° C for 12 h to obtain crude product 4-Methyl-2-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-benzonitrile.