Author/Authors :
Salmasi, Reihaneh Department of Chemistry - Faculty of Science - Ferdowsi University of Mashhad, Mashhad, Islamic Republic of Iran , Gholizadeh, Mostafa Department of Chemistry - Faculty of Science - Ferdowsi University of Mashhad, Mashhad, Islamic Republic of Iran , Salimi, Alireza Department of Chemistry - Faculty of Science - Ferdowsi University of Mashhad, Mashhad, Islamic Republic of Iran , Garrison, Jered C Department of Pharmaceutical Sciences - University of Nebraska Medical Center, Omaha, USA
Abstract :
1,2-Ethanediylbis(triphenylphosphonium) ditribromide was quantitatively prepared and used for the bromination of anilines and phenols in the presence of a mixed solvent system (DCM/MeOH 2:1) and also under solvent-free conditions. This new ionic liquid has advantages over similar brominating agents in terms of short reaction time, simple workup, regioselectivity and high yields. Single-crystal X-ray analysis of title salt revealed that the bistriphenylphosphonium cation is organized around an inversion center located at the center of the –CH2–CH2– bridge and the two triphenylphosphine segments are anti with respect to one another. All the tribromide anions adopt a linear geometry with different Br–Br–Br bond angles for each anion.
Keywords :
Bromination , Regioselectivity , Crystal structure , Nucleophilic substitutions , Solvent-free
