Ethyl Acetate → 7-Iodo-2-[3-(4-methoxy-phenyl)-propyl]-2,3-dihydro-isoindol-1-one

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Reaction Conditions

Reaction Steps

A mixture of 2-bromomethyl-6-iodo-benzoic acid methyl ester (0.245 g, 0.7 mmol), 3-(4-methoxy-phenyl)-propylamine (0.132 g, 0.8 mmol), and K2CO3 (0.207 g, 1.5 mmol) in toluene (5 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 7-iodo-2-[3-(4-methoxy-phenyl)-propyl]-2,3-dihydro-isoindol-1-one (0.125 g, 44%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.01 (m, 2H), 2.63 (t, 2H), 3.64 (t, 2H), 3.79 (s, 3H), 4.24 (s, 2H), 6.80 (d, 2H), 7.08-7.44 (m, 4H), 7.90 (d, 1H). GC-MS: m/z 407 (M)+.

Provenance & Evidence