Deethylation of Aryl Ethyl Ethers by Boron Tribromide

Abstract

Boron tribromide is well known as an effective reagent for cleaving methyl aryl ethers.^1,2 This procedure suffers from the unpredictable variability in the yield of the phenolic products arising from this cleavage.^lb While not reported as a preparative procedure, Egly et al.³ note that boron tribromide cleaves linear alkyl (up to chain length C₁₀) aryl ethers to yield, among a mixture of products, phenols, albeit in low yield.