Optical Resolution by Preferential Crystallization of (RS)-Bromosuccinic Acid

Abstract

Abstract The racemic structure of (RS)-bromosuccinic acid [(RS)-BSA] was examined based on the melting-point, solubility, infrared spectrum, and binary and ternary phase diagrams. The results indicated that (RS)-BSA exists as a conglomerate at room temperature, although it forms a racemic compound at the melting point. The optical resolution by preferential crystallization of (RS)-BSA yielded (R)- and (S)-BSA with optical purities of 81—93%. In addition, (RS)-BSA was optically resolved using (1S,2S)-2-amino-1-phenyl-1,3-propanediol as a resolving agent, to yield (R)- and (S)-BSA with optical purities of 99 and 83%, respectively. The obtained (R)- and (S)-BSA were recrystallized from water to obtain optically pure BSA enantiomers.