Reference of 766-81-4,Some common heterocyclic compound, 766-81-4, name is 3-Bromophenylacetylene, molecular formula is C8H5Br, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
General procedure: To a solution of 3-substituted-2-haloimidazo[4,5-b]pyridine derivative (1 equiv) in NMP, were added terminal acetylene (1.5 equiv) and tetrabutyl ammonium acetate (1.5 equiv). The solution was purged with nitrogen and stirred at room temperature for 0.15 h, at that time PdCl2(PCy3)2 was added. The reaction solution was purged again with nitrogen and then placed in the microwave and heated for 10 to 30 min at 110 C (for iodide and bromide intermediates). When chloro intermediate was used, the reaction contents were heated at 150 C. When TLC and LCMS showed full consumption of starting materials, the reaction mixture was diluted with ethyl acetate, separated the ethyl acetate layer, given water wash, brine wash and was dried over anhydrous sodium sulphate and concentrated to get the crude material. The crude product was directly purified by column chromatography (0-15% hexane/EtOAc) to isolate the 3-alkyl-2-akynyl imidao[4,5-b]pyridine derivatives.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromophenylacetylene, its application will become more common.
Reference:
Article; Sajith, Ayyiliath M.; Muralidharan; Tetrahedron Letters; vol. 53; 39; (2012); p. 5206 – 5210;,
Bromide – Wikipedia,
bromide – Wiktionary