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

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Reaction Conditions

Reaction Steps

A mixture of 4-chloro-2-bromomethyl-6-trifluoromethyl-benzoic acid methyl ester (1.33 g, 4.0 mmol), 4-trifluoromethoxy-benzylamine (0.610 mL, 4.1 mmol), and K2CO3 (0.691 g, 5.0 mmol) in toluene (10 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-chloro-2-(4-trifluoromethoxy-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.770 g, 47%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.34 (s, 2H), 4.80 (s, 2H) 7.20 (d, 2H), 7.36 (d, 2H), 7.59 (s, 1H), 7.78 (s, 1H). GC-MS: m/z 409 (M)+, 388 (M−21)+.

Provenance & Evidence