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

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Reaction Conditions

Reaction Steps

A mixture of 2-bromomethyl-6-chloro-benzoic acid methyl ester (0.132 g, 0.5 mmol), 4-chloro-benzylamine (0.073 g, 0.6 mmol), and K2CO3 (0.207 g, 1.5 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-chloro-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-1-one (0.116 g, 79%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.24 (s, 2H), 4.74 (s, 2H) 7.24-7.46 (m, 7H). GC-MS: m/z 291 (M)+.

Provenance & Evidence