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

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Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-bromomethyl-6-chloro-benzoic acid methyl ester (1.4 g, 4.0 mmol), 4-trifluoromethyl-benzylamine (0.770 mL, 5.4 mmol), and K2CO3 (1.1 g, 8.0 mmol) in toluene (10 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-bromo-7-chloro-2-(4-trifluoromethyl-benzyl)-2,3-dihydro-isoindol-1-one (0.553 g, 35%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.23 (s, 2H), 4.83 (s, 2H), 7.28-7.64 (m, 6H). GC-MS: m/z 405 (M+1)+, 336 (M−68)+.

Provenance & Evidence