Ethyl Acetate → 5,7-Dichloro-2-(4-difluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one

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Reaction Conditions

Reaction Steps

A mixture of 2-Bromomethyl-4,6-dichloro-benzoic acid methyl ester (0.150 g, 0.5 mmol), 4-difluoromethoxy-benzyl amine (0.101 g, 0.6 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 of the product using 30% ethyl acetate in hexane afforded 5,7-dichloro-2-(4-difluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.036 g, 20%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.22 (s, 2H), 4.74 (s, 214), 6.49 (t, 1H) 7.11 (d, 2H), 7.26-7.32 (m, 3H), 7.42 (s, 1H). GC-MS: m/z 357 (M)+.

Provenance & Evidence