A Green Route to Benzyl Phenyl Sulfide from Thioanisole and Benzyl Alcohol over Dual Functional Ionic Liquids.

ABSTRACT

Benzyl phenyl sulfide is a kind of important chemicals with wide usage, which is mainly prepared through a nucleophilic reaction of thiophenol with benzyl chlorides or benzyl alcohols, suffering from inherent drawbacks, such as low efficiency, requirements for equivalent acid or base catalysts and formation of harmful byproducts and waste. Herein, we report a green route to access various benzyl phenyl sulfide derivatives in good to excellent yields under mild conditions via the reaction of thioanisoles with benzyl alcohols over ionic liquid 1-propylsulfonate-3-methylimidazolium trifluoromethanesulfonate ([SO3 HPrMIm][OTf]). Mechanism investigation indicates that the synergic effect of cation and anion of [SO3 HPrMIm][OTf] activates thioanisoles and benzyl alcohols via hydrogen bonding, thus catalyzes the dehydration of benzyl alcohol to dibenzyl ether and the subsequent metathesis reaction between dibenzyl ether and benzyl phenyl sulfide, finally generating benzyl phenyl sulfide derivatives. This is a simple, highly efficient, and green approach to produce benzyl phenyl sulfide derivatives, which has promising application potentials.