Isolation of a 1,2-dihydrophenol derivative during an oxepin synthesis

Abstract

The reaction of t-butyl 4,5-epoxycyclohex-1-enecarboxylate (2) with N-bromosuccinimide produces a mixture of two pairs of epimeric bromides, (3) and (4), which react with triethylamine to give t-butyl oxepin-4-carboxylate (5)[from (3)] and with potassium t-butoxide to give t-butyl 5-bromo-2,3-dihydro-3-hydroxybenzoate (7)[from (4)].