1,2-Dibromotetrachloroethane: an efficient reagent for many transformations by modified Appel reaction

Abstract

An efficient and facile method has been developed for the synthesis of alkyl bromides from various alcoholsunder mild conditions using a triphenylphosphine (PPh 3)/1,2-dibromotetrachloroethane (DBTCE) complex in excellentyields and very short time (5 min). This method can also be applied for the transformation of chiral alcohols to theircorresponding bromides in very high enantiomeric excess. The PPh 3 /DBTCE complex is also successfully applied toring-opening reactions of cyclic ethers in mild conditions. Esterification, amidation, and formation of acid anhydridesunder very mild experimental conditions are also successfully accomplished by following a modification of the Appelreaction protocol in this work.