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

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Reaction Conditions

Reaction Steps

A mixture of 4-fluoro-2-bromomethyl-6-trifluoromethyl-benzoic acid methyl ester (0.100 g, 0.32 mmol), 4-chloro-benzylamine (0.051 mL, 0.42 mmol), and K2CO3 (0.088 g, 0.64 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 5-fluoro-2-(4-chloro-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.048 g, 44%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.28 (s, 2H), 4.75 (s, 2H) 7.24-7.51 (m, 6H). GC-MS: m/z 343 (M)+, 322 (M−21)+.

Provenance & Evidence