2-Methyl-2-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propionitrile synthesis

Yield:1160502-10-2 83%

Reaction Conditions:

with potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ in 1,2-dimethoxyethane at 100; for 0.5 h;

Steps:

2.2

A suspension of 2-(3-bromophenyl)-2-methylpropanenitrile (6.33 g, 28.25 mmol), bis(pinacolato)diboron (8.61 g, 33.90 mmol), potassium acetate (8.32 g, 84.80 mmol), 1 , 1 '-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (692 mg, 0.85 mmol), in ethylene glycol dimethyl ether (120 ml) was heated at 100⁰C under nitrogen for 30 minutes. The mixture was cooled down to room temperature, filtered through a path of celite and evaporated to dryness. The residue was purified on silica gel by flash column chromatography to afford the title compound as a white solid (6.39 g, 83% yield).¹H NMR (CD₃OD, 400 MHz) δ 1.37 (12H, s), 1.77 (6H, s), 7.42 (IH, t), 7.61 (IH, d), 7.79 (IH, d), 7.89 (IH, s); MS (ES⁺) 272.

References:

WO2009/73300,2009,A1 Location in patent:Page/Page column 108