Benzoyl Peroxide → 2-[4-(Chloromethyl)-2-pyridinyl]-1H-isoindole-1,3(2H)-dione

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Reaction Steps

A mixture of 2-(4-methyl-pyridin-2-yl)-isoindole-1,3-dione (952 mg, 4 mmol)), N-chloro succinimide (640 mg, 4.8 mmol), and benzoyl peroxide (484 g, 2 mmol) in carbon tetrachloride (20 ml) was refluxed for 2 hr. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, dichloromethane:EA (95:5)) to afford 300 mg (28%) of 2-(4-chloromethyl-pyridin-2-yl)-isoindole-1,3-dione as a pale brown solid. m.p. 152-153° C. 1H NMR (200 MHz, CDCl3) δ 4.64 (2H, s), 7.42 (1H, d, J=5.0 Hz), 7.49 (1H, s), 7.80-7.99 (4H, m), 8.68 (1H, d, J=5.0 Hz).

Provenance & Evidence