Bromobenzene → 1-Methoxy-5-phenoxynaphthalene

Participants

Reaction Steps

In a 3-neck flask fitted with a mechanical stirrer, 26.1 g of the 1-hydroxy-5-methoxynaphthalene prepared as above was treated with 16 ml bromobenzene, 41.4 g potassium carbonate, and 24.g of copper(I)oxide in 300 ml pyridine at reflux under argone. After 16 hours, an additional 3.2 mL of bromobenzene and 4.8 g of copper oxide were added and the reaction was continued for 4 hours. The reaction was cooled and filtered over supercel with an ethyl acetate washing. The combined filtrate was concentrated under vacuum, diluted with ethyl acetate, and shaken twice with cold dilute hydrochloric acid. The organic layer was dried over magnesium sulfate and evaporated under vacuum to an oil. The crude product was dissolved in 30 ml methylene chloride, and the resulting solution filtered and diluted with hexane to cloudiness. On cooling in the freezer, 3.98 g (11%) of crystalline 1-methoxy-5-phenoxynaphthalene was obtained.

Provenance & Evidence