A variety of 5,4-disubstituted flavones, which are anticipated to be androgen receptor antagonists to treat diseases mediated by the androgen receptor, were synthesized. It was found that an intramolecular ipso-substitution reaction via cesium enolate using 2-fluoro-6-hydroxyacetophenone and various benzoyl chlorides was effective in the preparation of 5-hydroxy-4-alkylflavones.
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