Ethyl Acetate → 7-Iodo-2-(4-methoxy-benzyl)-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), 4-methoxy-benzylamine (0.104 mL, 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-(4-methoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.084 g, 31%). 1H NMR (300 MHz, CDCl3): δ (ppm) 3.78 (s, 3H), 4.14 (s, 2H), 4.74 (s, 2H), 6.84 (d, 2H), 7.14-7.40 (m, 4H), 7.91 (d, 1H). GC-MS: m/z 379 (M)+.

Provenance & Evidence