Ammonia → 5-bromo-2,3-dihydro-1H-isoindol-1-one

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Reaction Steps

Methyl 4-bromo-2-(bromomethyl)benzoate (0.157 g, 0.510 mmol) was suspended in ammonia (2M solution in MeOH, 0.255 mL, 1.784 mmol). Ammonium hydroxide (0.517 mL, 7.65 mmol) was added and the mixture was stirred at RT overnight. A resulting white solid was collected by vacuum filtration, washed with water, and dried under high vacuum overnight to give the title compound as a white solid (0.066 g, 61%). 1H NMR (500 MHz, CDCl3) δ ppm 4.45 (s, 2 H), 6.35 (br s, 1 H), 7.60-7.68 (m, 2 H), 7.74 (d, J=8.30 Hz, 1 H); ESI-MS m/z [M+H]+ 212.3.

Provenance & Evidence