Sodium bromite,85%

• CAS: 7486-26-2
• Catalog Number: ALC-FP-7486262
• Category: Featured Products
• Molecular Weight: 134.89
• Molecular Formula: NaBrO2
• Appearance: Solid
• Sample Lot No.: A24C402E

Case Study

Sodium Bromite for Concomitant Bromination-Lactolisation of Unsaturated Diols

Evans GB, et al. Tetrahedron Letters, 1997, 38(26), 4709-4712.

Sodium bromite was applied as an efficient oxidative halogenating reagent for the concomitant bromination and lactolisation of unsaturated diols under mild acidic aqueous conditions. In a representative procedure, unsaturated diol substrates were dissolved in aqueous acetic acid and treated with sodium bromite at controlled temperature. The reaction proceeded smoothly, promoting electrophilic bromination of the olefinic bond while simultaneously inducing intramolecular cyclisation to form bromo lactols. This one-pot transformation avoided pre-functionalisation steps and demonstrated high chemoselectivity toward lactol formation. The resulting bromo lactols were isolated and subsequently oxidised using Jones reagent to afford the corresponding lactones in good yields, confirming the synthetic utility of the intermediate products. This methodology highlights sodium bromite as a versatile reagent capable of combining halogenation and oxidative cyclisation in a single step, offering a concise and experimentally practical route to functionalised lactols and lactones from unsaturated diols under aqueous conditions.

Sodium Bromite-Mediated Synthesis of Isoxazolines and Isoxazoles via Aldoxime Oxidation

Moriya O, et al. Tetrahedron Letters, 1989, 30(30), 3987-3990.

Sodium bromite was experimentally applied as a mild and efficient oxidant for the in situ generation of nitrile oxides from aldoximes, enabling the synthesis of isoxazolines and isoxazoles through dipolar cycloaddition. In a typical procedure, the aldoxime substrate was treated with sodium bromite in the presence of a catalytic amount of tributyltin chloride under controlled conditions. Sodium bromite selectively oxidized the aldoxime to the corresponding nitrile oxide intermediate without over-oxidation. The transient nitrile oxide was then directly trapped by alkynes or alkenes, affording isoxazoles or isoxazolines, respectively, in a one-pot transformation. The use of sodium bromite ensured smooth oxidation at relatively mild temperatures, minimizing side reactions and improving functional group tolerance. This methodology highlights sodium bromite's practical utility as an oxidizing reagent in heterocycle synthesis, particularly for constructing N-O containing five-membered rings via efficient, experimentally straightforward cycloaddition pathways.