Water → HCID 131720746, compound

Participants

Reaction Steps

A solution of n-butyllithium (2.5M, 53 mL, 0.133 mole) was added dropwise over 30 minutes under argon to a solution of 1,4-dibromobenzene (30.0 g, 0.127 mole) in dry THF (575 mL) at -78° C. After stirring for 1.5 h, bromomethylchlorodimethylsilane (25.0 g, 0.133 mole) was added to the reaction mixture through a canula and the solution was stirred for 1.5 h at -78° C. The reaction was poured into water (325 mL) and extracted with ether. The combined extracts were washed with water and brine, and then dried (Na2SO4) and concentrated in vacuo to an oil. The oil was distilled (Kugelrohr, 110°-125° C., 0.05 mm Hg) to afford the compound as a clear, colorless oil (22.6 g, 58%). 1H NMR (400 MHz, CDCl3) 7.45 (dd, 4H), 2.60 (s, 2H), 0.45 (s, 6H).

Provenance & Evidence