Dimethylformamide → 3-Bromo-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzonitrile

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Reaction Steps

A suspension of 3-bromo-5-(bromomethyl)benzonitrile (12.5 g, 45.5 mmol), potassium phthalate (7.16 g, 38.6 mmol), and in DMF (100 mL) was stirred under reflux for 4 h. After cooling to room temperature, the solvent was remove under reduced pressure and the residue was dissolved in CHCl3 (200 mL). The organic layer was washed with water (50 mL×2), dried over Na2SO4, and concentrated in vacuum to obtain 15.2 g of the crude product. The product, 3-bromo-5-[(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)methyl]benzonitrile (3.50 g, 23%) was purified by flash column chomatography. 1H NMR (400 MHz, CDCl3) δ 7.90-7.87 (m, 2H), 7.81-7.80 (m, 1H), 7.77-7.75 (m, 2H), 7.71-7.70 (m, 1H), 7.66-7.65 (m, 1H), 4.83 (s, 2H).

Provenance & Evidence