449204-48-2Relevant academic research and scientific papers
Deprotection of acetals from unsaturated, unstable bromoketones
Descomps, Alexandre,Carlson, Rolf
, p. 757 - 761 (2014)
The unstable ketones 1-bromo-3-buten-2-one, 1-bromo-3-butyn-2-one, and 1,3-dibromo-3-buten-2-one can be obtained from the corresponding acetals in high yields by treating the acetals with anhydrous iron (III) chloride suspended on dry silica. A simplified procedure for preparing the reagent is also given.
Synthesis of 1-bromo-3-butyn-2-one and 1,3-dibromo-3-buten-2-one
Mekonnen, Alemayehu,Westerlund, Andreas,Havelkova, Martina,Descomps, Alexandre,Carlson, Rolf
experimental part, p. 2472 - 2480 (2009/12/06)
Synthetic procedures for the preparation of 1-bromo-3-butyn-2-one and 1,3-dibromo-3-buten-2-one are given. These compounds are prepared from 2-bromomethyl-2-vinyl-1,3-dioxolane, which can readily be prepared from 2-ethyl- 2-methyl-1,3-dioxolane. The synthetic routes are as follows: 2-bromomethyl-2-vinyl-1,3-dioxolane is converted to2-(1,2-dibromoethyl)-2- bromomethyl-1,3-dioxolane. Double dehydrobromination with tBuOK affords 2-ethynyl-2-bromomethyl-1,3-dioxolane. Formolysis with formic acid gives 1-bromo-3-butyn-2-one. Deacetalized 2-bromoethyl-2-vinyl-1,3-dioxolane was treated with Br2 and Li2CO3/12-crown-4 in tetrahydrofuran to give 1,3-dibrom-3-buten-2-one in moderate yield.
