1,2-Dibromoethyltrimethylsilane synthesis

Yield:18146-08-2 92%

Reaction Conditions:

with NBS;benzamide in acetonitrile at 20; for 20 h;

Steps:

2.2.7. Reaction of carboxamides with trimethyl(vinyl)silane in the presence of NBS in MeCN

To the solution of 1.00 g (17 mmol) of acetamide (or 1.00 g (8.3 mmol) of benzamide) and 3.02 g (17 mmol) of NBS (or 1.47 g (8.3 mmol) in the reaction with benzamide) in 60 ml of MeCN 2.75 ml (17 mmol) (or 1.34 ml (8.3 mmol) in the reaction with benzamide) of trimethyl(vinyl)silane 1 was added and the mixture kept for 20 h at room temperature. After completion, MeCN was removed in vacuum, the residue dissolved in 70 ml of ether, Nsuccinimide filtered off, the filtrate evaporated, the residue (2.0- 3.1 g) separated on a silica column with hexane and hexane-ether 1:1 as eluents. From the hexane eluate, 3.02 g (69%) and 1.98 g (92%) of (1,2-dibromoethyl)trimethylsilane 15a was isolated as colorless liquid, and from hexane-ether eluate the unreacted carboxamide was obtained.

References:

Astakhova, Vera V.;Moskalik, Mikhail Yu.;Shainyan, Bagrat A. [Journal of Organometallic Chemistry,2022,vol. 960,art. no. 122230]