Tetraethylammonium fluoride in dimethylformamide promotes the alkylation of phenols with alkyl iodides and benzyl chloride to provide good yields of alkyl phenyl ethers. A number of phenols have been investigated including examples of sterically hindered phenols, phenols containing anion stabilising groups, and intramolecularly hydrogen bonded phenols, the majority of which react smoothly and efficiently in the fluoride system.
