Benzylamine → 2-Benzyl-5-bromo-2,3-dihydro-1H-isoindol-1-one

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Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-bromomethyl-benzoic acid methyl ester (0.308 g, 1.0 mmol), benzylamine (0.218 mL, 2.0 mmol), and K2CO3 (0.553 g, 4.0 mmol) in toluene (6 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 2-benzyl-5-bromo-2,3-dihydro-isoindol-1-one (0.150 g, 50%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.22 (s, 2H), 4.76 (s, 2H), 7.21-7.38 (m, 5H), 7.52 (s, 1H), 7.61 (d, 1H), 7.76 (d, 1H). GC-MS: m/z 302 (M)+, 226 (M−76)+.

Provenance & Evidence