Ethyl Acetate → 7-Iodo-2-(4-butyl-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 (0.107 g, 0.3 mmol), 4-butyl-benzylamine (0.088 mL, 0.5 mmol), and K2CO3 (0.083 g, 0.6 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-butyl-benzyl)-2,3-dihydro-isoindol-1-one (0.063 g, 50%). 1H NMR (300 MHz, CDCl3): δ (ppm) 0.88 (t, 3H), 1.34 (m, 2H), 1.56 (m, 2H), 2.58 (t, 2H), 4.16 (s, 2H), 4.76 (s, 2H), 7.14-7.36 (m, 6H), 7.85 (d, 1H). GC-MS: m/z 405 (M)+, 348(M−57)+.

Provenance & Evidence