Phenol → HCID 20032362, compound

Participants

Reaction Steps

To a mixture of 0.6 g (0.0016 mole) of N-(4-chloro-2-fluoro-5-bromomethylphenyl)-3,4,5,6-tetrahydrophthalimide and 0.22 g (0.0016 mole) of potassium carbonate in acetone was added 0.15 g (0.0016 mole) of phenol. The mixture was stirred overnight at room temperature and then was heated at 50° C. for approximately 24 hours. The reaction mixture was filtered, and the filter cake was washed with ethyl acetate. The filtrate was washed with water, dried, and the solvent was evaporated under reduced pressure, leaving a residue weighing 0.7 g. Preparative thin layer chromatography was used to separate the components of this residue, eluting with ethyl acetate/heptane (3/7). The product, 0.18 g of N-(4-chloro-2-fluoro-5-phenoxymethylphenyl)-3,4,5,6-tetrahydrophthalimide, was isolated as an oil. The nmr and ir were consistent with the proposed structure.

Provenance & Evidence