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. 2021 Apr 16;11(24):14453-14458.
doi: 10.1039/d1ra01980e. eCollection 2021 Apr 15.

Bromotrimethylsilane as a selective reagent for the synthesis of bromohydrins

Donatella Giomi  1   2 , Antonella Salvini  1   2 , Jacopo Ceccarelli  1 , Alberto Brandi  1   2
Affiliations

Bromotrimethylsilane as a selective reagent for the synthesis of bromohydrins

Donatella Giomi et al. RSC Adv. .

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.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Sunflower oil and castor oil (ricinolein).
Scheme 1
Scheme 1. Transesterification of castor oil (2) with TMSBr.
Scheme 2
Scheme 2. Role of TMSBr as mediator for transesterification of triglycerides.
Scheme 3
Scheme 3. Side processes involving TMSBr decomposition.
Fig. 2
Fig. 2. (a) Experiments performed at 60 °C (Table 2, entries 2 and 3). (b) Experiments performed at 20 °C (Table 2, entries 5 and 6).
Scheme 4
Scheme 4. Bromination of glycerol with TMSBr.
Scheme 5
Scheme 5. Reaction pathway for bromohydrins formation.
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