Finding safer replacements for dichloromethane: MCPBA epoxidation of alkenes in BTF and 2-MeTHF

The U.S. Environmental Protection Agency (EPA) has placed a ban on most uses of dichloromethane (CH 2 Cl 2 ) due to its highly toxic and carcinogenic nature. Several deaths have been attributed to CH 2 Cl 2 exposure. Unfortunately, CH 2 Cl 2 has been one of the most commonly used solvents in synthetic chemistry. For example, the peracid epoxidation of alkenes is typically carried out in dichloromethane as the solvent. With the goal of finding safer alternatives to CH 2 Cl 2 , we chose the MCPBA epoxidation of alkenes as a test reaction and explored the utility of benzotrifluoride (BTF) and 2-methyltetrahydrofuran (2-MeTHF) as solvents. Herein, we report the use of BTF and 2-MeTHF as viable alternatives to CH 2 Cl 2 for the MCPBA epoxidation of alkenes.