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Zwitterionic Hydrobromic Acid Carriers for the Synthesis of 2‐Bromopropionic Acid from Lactide
Author(s) -
Kehrer Matthias,
Mehler Julian,
Taccardi Nicola,
Nagengast Jens,
Kadar Julian,
Collias Dimitris,
Dziezok Peter,
Wasserscheid Peter,
Albert Jakob
Publication year - 2018
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201702369
Subject(s) - ionic liquid , halogenation , chemistry , hydrobromic acid , bromide , selectivity , ammonium bromide , solvent , substrate (aquarium) , ammonium , catalysis , organic chemistry , pulmonary surfactant , biochemistry , oceanography , geology
A convenient and highly efficient way of synthesizing 2‐bromopropionic acid (2‐BrPA) from lactide is presented. The procedure uses ionic liquids obtained from the addition of HBr to ammonium‐based zwitterions as the solvent and bromination agent. The buffered HBr acidity, high polarity, and charge stabilizing character of the ionic liquid (IL) enable the synthesis of 2‐BrPA with excellent selectivity. The best results are obtained with an imidazolium‐based IL, that is, 1‐(4‐butanesulfonic acid)‐3‐methylimidazolium bromide ([MIMBS]Br). The HBr loading and water content of the IL are crucial parameters for the bromination reaction. The formed 2‐BrPA product can be selectively isolated by extraction from the IL, and the unconverted substrate remains in the [MIMBS]Br IL for the next run. Successful recycling of the IL over four cycles is demonstrated.