Potassium Carbonate → 5-Fluoro-7-iodo-2-(4-cyano-benzyl)-2,3-dihydro-isoindol-1-one

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Reaction Conditions

Reaction Steps

A mixture of 4-cyano-benzyl amine (0.218 g, 1.3 mmol), 2-bromomethyl-4-fluoro-6-iodo-benzoic acid methyl ester (0.374 g, 1.0 mmol), and K2CO3 (0.277 g, 2 mmol) in toluene (4 mL) was heated with stirring at 100° C. for 2 h. The resulting mixture was filtered and concentrated. Silica gel column chromatography using 30% ethyl acetate in hexane afforded 5-fluoro-7-iodo-2-(4-cyano-benzyl)-2,3-dihydro-isoindol-1-one (0.160 g, 41%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.19 (s, 2H), 4.83 (s, 2H), 7.13 (d, 1H), 7.42 (d, 2H), 7.64 (m, 3H). GC-MS: m/z 392 (M)4.

Provenance & Evidence