Bromotrimethylsilane as a selective reagent for the synthesis of bromohydrins

• Published in: RSC advances Vol. 11; no. 24; pp. 14453 - 14458
• Main Authors: Giomi, Donatella, Salvini, Antonella, Ceccarelli, Jacopo, Brandi, Alberto
• Format: Journal Article
• Language: English
• Published: England Royal Society of Chemistry 16.04.2021; The Royal Society of Chemistry
• Subjects: biodiesel; Biodiesel fuels; byproducts; Castor oil; Chemistry; Conversion; Fine chemicals; Glycerol; NMR; Nuclear magnetic resonance; Reagents; Transesterification
• ISSN: 2046-2069; 2046-2069
• DOI: 10.1039/d1ra01980e

Bromotrimethylsilane (TMSBr) is a very efficient reagent in the solvent-free conversion of glycerol into bromohydrins, useful intermediates in the production of fine chemicals. As glycerol is a relevant by-product in biodiesel production, TMSBr has been also tested as a mediator in transesterification in acidic conditions, providing FAME from castor oil in good yields, along with bromohydrins from glycerol. Subsequently the glycerol conversion was optimized and depending on the reaction conditions, glycerol can be selectively converted into α-monobromohydrin (1-MBH) or α,γ-dibromohydrin (1,3-DBH) in very good yields. Glycerol, a by-product of biodiesel production, can be efficiently converted into α-monobromohydrin or α,γ-dibromohydrin with trimethylsilyl bromide (TMSBr), in solvent-free and mild reaction conditions.