KHSO₄-Catalyzed Synthesis of 1,1′-Oxybis(2-bromoethane-1,1-diyl)dibenzenes and 1-(1-(Benzyloxy)-2-bromoethyl)benzenes Under Solvent-Free Conditions

Abstract

An economical and green conversion of 2-bromo-1-phenylethanols and benzylic alcohols into 1,1′-oxybis(2-bromoethane-1,1-diyl)dibenzenes and 1-(1-(benyloxy)-2-bromomethy)benzenes catalyzed by KHSO₄ under neat condition is described. The present protocol is facile and chemoselective without transition-metal catalyst/solvent, and the KHSO₄ catalyst is recyclable.

GRAPHICAL ABSTRACT

Keywords:

• Benzylic alcohols
• 2-bromo-1-phenylethanol
• dibenzenes
• KHSO₄
• solvent free

ACKNOWLEDGMENTS

We thank Mr. Hitesh, Mr. A. K. Das, and Mr. H. Brahmbhatt, and Mr. V. Agrawal of our Analytical Division for supporting NMR, mass, IR, and elemental analyses respectively. G. J. is thankful to the Council of Scientific and Industrial Research, New Delhi, India, for the award of a senior research fellowship.

Notes

^a Conditions: 1 (5 mmol), catalyst (10 mol%), solvent free.

^b Isolated yield.

^c 5 mol% catalyst was used.

^d 7 mol% catalyst was used.

^e Trace product was obtained.

^f 1 (reaction conducted at 13.9-mmol scale).

^a Conditions: 1 (5 mmol), catalyst (10 mol%), solvent free.

^b Isolated yield.

^c Catalyst (10 mol%), reaction time 10 h.

^a Conditions: 1 (5 mmol), catalyst (10 mol%), solvent free.

^b Isolated yield.

^c Including 12% mixture of homo coupled products 2 and 4a.