Synthesis
Add (3-bromophenyl)triphenylsilane (72.0g, 173 mmol) and THF (1576 ml) to a 5L flask. The resulting reaction mixture was stirred and cooled to -78°C. A solution of hexyllithium in hexane (2.3M, 113ml, 260mmol) was added over 20 minutes and stirred for 45 minutes. Then, slowly add a solution of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (60.1ml, 295mmol) in THF (158ml), And the reaction mixture was warmed to room temperature and stirred overnight (about 16 hours). The reaction mixture was quenched with ice-cold water (1 L), and the organic layer was separated. The aqueous layer was extracted with EtOAc (2×700 mL), and the combined organic layer was dried over Na2SO4, filtered, and concentrated. The off-white solid was wet-milled with heptane (500 mL) to obtain triphenyl[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]silane as a white solid (64.97g).
