Ethyl Acetate → [6-Fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester

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To a mixture of 4-fluoro-2-(4-methanesulfonyl-phenylethynyl)-benzaldehyde (1.74 g, 5.77 mmol) and gold(III) bromide (0.15 g, 0.35 mmol) in dioxane (8 mL) was added 4-oxo-butyric acid ethyl ester (1.50 g, 11.53 mmol). The reaction mixture was heated at 100° C. under nitrogen for 4 hours. The solvent was removed in vacuo to afford a deep red viscous oil. Flash chromatography (RediSep® Flash column, 230-400 mesh, 25-65% ethyl acetate in hexane) gave [6-fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid ethyl ester (0.63 g, 26%). MS (ESI+) cald. for C22H19FO5S [(M+H)+] 414, obsd. 415. It is noted that in some instances, this reaction also produced some amount of [6-fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid.

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