N-Benzyl-DABCO Tribromide

Introduction

Organic ammonium tribromides are of high molecular weight, stable, crystalline solids, and capable to release a stoichiometric amount of bromine (where small quantities of bromine are necessary for microscale reactions). [¹] N-Benzyl-DABCO tribromide (NBDTB) is an efficient, stable, and cheap solid reagent, which is quite soluble in methanol, dichloromethane, and dimethylsulfoxide, but insoluble in most nonpolar or less polar solvents, such as n-hexane and diethyl ether.^² N-Benzyl-DABCO tribromide can be readily prepared from DABCO and benzyl bromide, followed by treatment with liquid bromine. [³]

Scheme 1

References

• 1a Jordan AD. Luo C. Reitz AB. J. Org. Chem.  2003,  68:  8693 
• 1b Bakavoli M. Motavalizadeh Kakhky A. Shiri A. Ghabdian M. Davoodnia A. Eshghi H. Khatami M. Chin. Chem. Lett.  2010,  21:  651 
• 1c Bakavoli M. Rahimizadeh M. Eshghi H. Ebrahimpour Z. Takjoo R. Bull. Korean Chem. Soc.  2010,  31:  949 
• 2 Moghaddam MF. Zargarani D. Synth. Commun.  2009,  39:  4212 
• 3 Boeini HZ. J. Iran. Chem. Soc.  2009,  6:  547 
• 4 Moghaddam MF. Boeini HZ. Synlett  2005,  1612 
• 5 Moghaddam MF. Boeini HZ. Zargarani D. Bardajee GR. Synth. Commun.  2005,  36:  1093 
• 6 Moghaddam MF. Zargarani D. Boeini HZ. Synth. Commun.  2008,  38:  1694