Ethyl Acetate → 7-Chloro-2-[1-(4-chloro-phenyl)-ethyl]-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), 1-(4-chlorophenyl)-ethylamine (0.117 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-[1-(4-chloro-phenyl)-ethyl]-2,3-dihydro-isoindol-1-one (0.132 g, 86%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.66 (d, 3H), 3.95 (d, 1H), 4.34 (d, 1H), 5.84 (q, 1H) 7.26-7.46 (m, 7H). GC-MS: m/z 306 (M)+.

Provenance & Evidence