Ortho-metalation of p-chloroanisole: A media study

Article abstract of DOI:10.1016/S0040-4039(99)00161-6

As the chlorophenyl group is a pharmacophore, its stability toward metalation conditions in conjunction with the methoxy substituent was assessed. For p-chloroanisole metalation ortho to the methoxy group was achieved in high yield using increments of THF in cyclohexane; numerous other regimes afforded lower yields and a competing benzyne pathway.