Ethyl Acetate → HCID 11717332, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-2-bromomethyl-6-trifluoromethyl-benzoic acid methyl ester (0.995 g, 3.0 mmol), 4-ethyl-benzylamine (0.520 mL, 3.6 mmol), and K2CO3 (0.621 g, 4.5 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-chloro-2-(4-ethyl-benzyl)-7-trifluoromethyl-2,3-dihydro-isoindol-1-one (0.30 g, 28%). 1H NMR (300 MHz, CDCl3): δ (ppm) 1.24 (t, 3H), 2.63 (q, 2H), 4.27 (s, 2H), 4.76 (s, 2H) 7.20 (m, 4H), 7.59 (s, 1H), 7.78 (s, 1H). GC-MS: m/z 353 (M)+, 338 (M−15)+, 324 (M−29)+.

Provenance & Evidence