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

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Reaction Conditions

Reaction Steps

A mixture of 4-trifluoromethoxy-benzyl amine (0.092 mL, 0.6 mmol), 2-bromomethyl-4-fluoro-6-iodo-benzoic acid methyl ester (0.181 g, 0.49 mmol), and K2CO3 (0.138 g, 1 mmol) in toluene 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-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.080 g, 36%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.19 (s, 2H), 4.79 (s, 2H), 7.06-7.38 (m, 5H), 7.67 (d, 1H). GC-MS: m/z 451 (M)+, 382 (M−69)+.

Provenance & Evidence