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

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-fluoro-2-bromomethyl-6-trifluoromethyl-benzoic acid methyl ester (0.100 g, 0.32 mmol), 4-ethyl-benzylamine (0.06 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-ethyl-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.36 g, 33%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.22 (t, 3H), 2.65 (q, 2H), 4.27 (s, 2H), 4.78 (s, 2H) 7.20-7.56 (m, 6H). GC-MS: m/z 337 (M)+, 318 (M−19)+.

Provenance & Evidence