1-(2-hydroxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ethanone synthesis

Yield:1246560-24-6 69%

Reaction Conditions:

with (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;potassium acetate in 1,4-dioxane at 0 - 80;

Steps:

4.1.3 General synthesis of boronic pinacol esters

General procedure: Into a thick walled screw top flask containing a solution of appropriately substituted aryl halide (2.49mmol, 1eq) in dry 1,4-dioxane (10ml) were added bis(pinacolato)diboron (0.632g, 2.49mmol, 1eq) [1,1′-Bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.03eq) and potassium acetate (3eq). The flask was cooled to 0°C under argon for 30min. The reaction mixture was gradually warmed to room temperature, and stirred at 80°C for 16h. After cooling to room temperature, the solvent was evaporated to dryness under reduced pressure. The residue was dissolved in n-hexane, and the solution was washed with H₂O, brine and dried (MgSO₄), further purification was by recrystallization from hexane.

References:

Barnes, Natalie G.;Parker, Anthony W.;Ahmed Mal Ullah, Amjed A.;Ragazzon, Patricia A.;Hadfield, John A. [Bioorganic and Medicinal Chemistry,2020,vol. 28,# 19,art. no. 115684]