2-Methylbenzylamine → 7-Iodo-2-(2-methyl-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), 2-methyl-benzylamine (0.063 mL, 0.5 mmol), and K2CO3 (0.138 g, 1.0 mmol) in toluene (4 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-(2-methyl-benzyl)-2,3-dihydro-isoindol-1-one (0.056 g, 51%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.35 (s, 3H), 4.14 (s, 2H), 4.82 (s, 2H), 7.11-7.38 (m, 6H), 7.91 (d, 1H). GC-MS: m/z 363 (M)+.

Provenance & Evidence