Nitric Acid → 4-Bromo-2-methyl-7-nitroisoindolin-1-one

Participants

Reaction Conditions

Reaction Steps

To a cold suspension of 4-bromo-2-methyl-2,3-dihydroisoindol-1-one (60 g, 265 mmol) in concentrated sulfuric acid (60 mL) was added pre-cooled mixture of conc. nitric acid (12.5 mL, 265 mmol) and conc. sulfuric acid (60 mL) over 20 min. The reaction mixture was stirred for 30 min at 0° C. and 2 h at room temperature. The reaction mixture was poured over ice-water mixture (300 mL). The precipitate was filtered, washed with water (3×100 mL) and suspended in isopropanol (200 mL). The slurry was heated on steam bath and cooled. The solid was filtered and dried in air to give 53 g (74%) of the title compound. 1H NMR (CDCl3, 300 MHz) δ 3.22 (s, 3H), 4.36 (s, 2H), 7.67 (d, J=8.4 Hz, 1H), 7.78 (d, J=8.4 Hz, 1H).

Provenance & Evidence