Preparation and properties of a novel solution of hydrogen bromide (HBr) in 1,4-dioxane: An alternative reagent to HBr gas without protic solvents

• Published in: Tetrahedron letters Vol. 58; no. 12; pp. 1190 - 1193
• Main Authors: Nishio, Yuya, Mifune, Ryota, Sato, Taisuke, Ishikawa, Shin-ich, Matsubara, Hiroshi
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 22.03.2017; Elsevier
• Subjects: 1,3-Dioxolane; 1,4-Dioxane; Bromination of alcohols; Chemistry; Chemistry, Organic; Hydrobromination of alkenes; Hydrogen bromide solution; Physical Sciences; Science & Technology; Hydrobromination of alkenes; Bromination of alcohols; 1,3-Dioxolane; Hydrogen bromide solution; 1,4-Dioxane; PHASE-SCREEN; BROMINATION; ACID; N-BROMOSUCCINIMIDE; OLEFINS
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2017.02.020

[Display omitted] •A novel solution of HBr in 1,4-dioxane was prepared.•Bromination of ROH and hydrobromination of alkenes were examined with the solution.•The novel solution provided equal or superior results to HBraq and HBr/AcOH.•Preparation of dioxolanes and dioxanes was achieved using the novel solution.•The novel solution is a liquid alternative to HBr gas without protic solvents. A solution of hydrogen bromide (HBr) in 1,4-dioxane was prepared and investigated for its ability to brominate alcohols, and hydrobrominate alkenes. This study revealed that the brominating ability of this HBr/1,4-dioxane solution is equal or superior to that of hydrobromic acid or HBr in acetic acid. The solution of HBr in 1,4-dioxane is robust, exhibiting no decomposition of the solvent, and retaining 97% of its original concentration, when kept at −25°C for 30days. This solution is a liquid alternative to HBr gas without protic solvents.