Ethyl Acetate → 5-Bromo-7-methyl-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-1-one

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Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-bromomethyl-6-methyl-benzoic acid methyl ester (0.966 g, 3.0 mmol), 4-chloro-benzylamine (0.462 mL, 3.8 mmol), and K2CO3 (0.829 g, 6.0 mmol) in toluene (10 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 5-bromo-7-methyl-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-1-one (0.725 g, 69%). GC-MS: m/z 350 (M)+, 314 (M−36)+.

Provenance & Evidence