Water → 4-(2-Hydroxy-2-methylpropoxy)-3-methoxyphenylboronic acid

Participants

Reaction Steps

To a solution of 1-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-2-methylpropan-2-ol Part B (0.880 g, 2.73 mmol) in acetone (20 mL) and water (20 mL) was added sodium periodate (2.3 g, 10.92 mmol) and ammonium acetate (0.84 g, 10.92 mmol). The mixture stirred at RT overnight. Filtered the white solids, washed the filter cake with acetone and removed the acetone. The product was then extracted with EtOAc, and brine, and, dried (MgSO4), concentrated to afford the crude product. Residue was purified using ISCO flash chromatography (silica gel/methylene chloride-methanol 100:0 to 85:15 gradient) to afford the desired product 4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenylboronic acid 9C (0.443 g, 1.845 mmol, 67.6% yield) as a light brown solid.

Provenance & Evidence