Ammonia → (2-(4-(5-Bromo-2-chlorobenzyl)phenyl)ethynyl)triisopropylsilane

Participants

Reaction Conditions

Reaction Steps

Under argon 0.66 ml of a 2 M solution of isopropylmagnesium chloride in tetrahydrofuran are added dropwise to a solution of 0.50 g (4-iodo-phenylethynyl)-triisopropyl-silane in 2.2 mL dry tetrahydrofuran chilled to −25° C. The solution is stirred for 30 min at−25° C. and then combined with 0.26 mL of a 1 M solution of CuCN*2 LiCl in tetrahydrofuran (prepared by dissolving CuCN and LiCl in the ratio 1:2). Shortly afterwards, 0.35 g 4-bromo-2-bromomethyl-1-chloro-benzene are added and the reaction mixture is warmed up to −5° C. in the cooling bath. After 6 h stirring at −5° C., the solution is warmed to ambient temperature and stirred overnight. Then a mixture of saturated ammonium chloride solution and 25% ammonia solution (9:1) is added, and the resulting mixture is added to water. The organic phase is separated, the aqueous phase is extracted with ethyl acetate, the combined organic phases are dried over sodium sulfate, and the solvent is removed. The residue is purified through silica gel (cyclohexane).

Provenance & Evidence