Acetonitrile → 7-chloro-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-7-chloro-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.349 g, 0.83 mmol), Pd(PPh3)4 (0.317 g, 0.25 mmol), sodium cyanide (0.048 g, 0.946 mmol), CuI (0.016 g, 0.086 mmol), acetonitrile (4 mL) was stirred at 80° C. for 18 h. Workup and silica gel column chromatography using 2:1 hexanes-ethyl acetate (typically 2:1 hexane-EtOAc) afforded 7-chloro-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carbonitrile (0.100 g, 33%). 1H NMR (300 MHz, CDCl3): δ (ppm) 4.32 (s, 2H), 4.79 (s, 2H), 7.20 (d, 2H), 7.35 (d, 2H), 7.58 (s, 1H), 7.70 (s, 1H). GC-MS: m/z 366 (M−1)+, 281 (M−85)+.

Provenance & Evidence