Aniline → 5-Bromo-2-phenyl-2,3-dihydro-1H-isoindol-1-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl 4-bromo-2-(bromomethyl)benzoate (0.204 g, 0.662 mmol) in MeOH (5.5 mL) were added aniline (0.063 mL, 0.696 mmol) and Et3N (0.144 mL, 1.027 mmol). The mixture was heated to reflux (85° C.) for 24 hours and subsequently cooled. A white solid that formed was collected by vacuum filtration, rinsed with MeOH, and dried under vacuum to give the title compound as a white solid (0.138 g, 72% yield). 1H NMR (500 MHz, CDCl3) δ ppm 3.89 (s, 2 H), 4.85 (s, 2 H), 7.15-7.24 (m, 1 H), 7.40-7.52 (m, 2 H), 7.62-7.96 (m, 5 H); ESI-MS m/z/[M+H]+ 288.3.

Provenance & Evidence