Potassium Acetate → HCID 89582740, compound

Participants

Reaction Steps

4-(4-Iodophenoxy)-2-trifluoromethyl benzonitrile (20 g, 51.4 mmol) was treated with bis-pinacol boronate (13 g, 51.4 mmol, NetChem), KOAc (10 g, 102.8 mmol), and PdCl2dppf*CH2Cl2 (2.1 g, 2.57 mmol) in 50 mL dioxane at 100° C. for 20 hours. The reaction mixture was diluted with 500 mL water and extracted with 2×300 mL EtOAc. The combined organic layers were washed with 250 mL brine, dried over sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on silica using a gradient of EtOAc (20% max) in hexane as the eluent to give 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)-2-(trifluoromethyl)benzonitrile (11.45 g, 57%). 1H NMR (400 MHz, CDCl3): 7.93-7.86 (2 H, m), 7.79-7.71 (1 H, m), 7.36-7.32 (1 H, m), 7.17-7.12 (1 H, m), 7.10-7.04 (2 H, m), 1.38-1.34 (12 H, s).

Provenance & Evidence