Benzylamine → 2-Benzyl-6-fluoro-2,3-dihydro-isoindol-1-one

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Reaction Conditions

Reaction Steps

A mixture of 2-bromomethyl-5-fluoro-benzoic acid methyl ester (0.094 g, 0.5 mmol), benzylamine (0.076 mL, 0.7 mmol), and K2CO3 (0.207 g, 1.5 mmol) in toluene (5 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-6-fluoro-2,3-dihydro-isoindol-1-one (0.085 g, 70.7%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.24 (s, 2H), 4.79 (s, 2H), 7.18-7.39 (m, 7H), 7.55 (m, 1H). GC-MS: m/z 241 (M)+, 164 (M−77)+.

Provenance & Evidence