Bromotrimethylsilane as a selective reagent for the synthesis of bromohydrins.

Donatella Giomi, Antonella Salvini, Jacopo Ceccarelli, Alberto Brandi
Author Information
  1. Donatella Giomi: Dipartimento di Chimica 'Ugo Schiff', Università degli Studi di Firenze Via della Lastruccia 3-13 I-50019 Sesto Fiorentino (Fi) Italy donatella.giomi@unifi.it antonella.salvini@unifi.it. ORCID
  2. Antonella Salvini: Dipartimento di Chimica 'Ugo Schiff', Università degli Studi di Firenze Via della Lastruccia 3-13 I-50019 Sesto Fiorentino (Fi) Italy donatella.giomi@unifi.it antonella.salvini@unifi.it. ORCID
  3. Jacopo Ceccarelli: Dipartimento di Chimica 'Ugo Schiff', Università degli Studi di Firenze Via della Lastruccia 3-13 I-50019 Sesto Fiorentino (Fi) Italy donatella.giomi@unifi.it antonella.salvini@unifi.it. ORCID
  4. Alberto Brandi: Dipartimento di Chimica 'Ugo Schiff', Università degli Studi di Firenze Via della Lastruccia 3-13 I-50019 Sesto Fiorentino (Fi) Italy donatella.giomi@unifi.it antonella.salvini@unifi.it. ORCID

Abstract

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.

References

  1. Chem Commun (Camb). 2020 Mar 17;56(22):3309-3312 [PMID: 32076697]
  2. Biotechnol Biofuels. 2012 Mar 14;5:13 [PMID: 22413907]
  3. Molecules. 2020 Jan 05;25(1): [PMID: 31948129]
  4. Bioresour Technol. 2004 May;92(3):297-305 [PMID: 14766164]
  5. Front Chem. 2020 Feb 11;8:69 [PMID: 32117892]

Word Cloud

Created with Highcharts 10.0.0glycerolbromohydrinsBromotrimethylsilaneTMSBrreagentconversionproductionconditionsgoodyieldsefficientsolvent-freeusefulintermediatesfinechemicalsrelevantby-productbiodieselalsotestedmediatortransesterificationacidicprovidingFAMEcastoroilalongSubsequentlyoptimizeddependingreactioncanselectivelyconvertedα-monobromohydrin1-MBHαγ-dibromohydrin13-DBHselectivesynthesis

Similar Articles

Cited By

No available data.