3-(Bromomethyl)-5-methylbenzonitrile → Phthalimide

関与物質

反応手順

A mixture of 3-cyano-5-methylbenzyl bromide from Example 7, Step 1 (15.79 g, 75.16 mmol) and potassium phthalimide (15.31 g, 82.68 mmol) in N,N-dimethylformamide (150 mL) was vigorously stirred for 4 hours. The reaction mixture was freed of solvent and the residue was dissolved in chloroform (200 mL)/water (400 mL). The chloroform fraction was separated and the aqueous phase was extracted with chloroform (2×75 mL). The combined chloroform fractions were washed with water, with brine and dried (anhydrous Na2SO4). Removal of solvent gave 20.2 g of crude product which was recrystallized from acetonitrile to yield 13.12 g (63%) of white phthalimide: mp 180°-184° C.; 1H NMR (DMSO-d6) δ7.87 (br m, 4H), 7.60 (s, br, 1H), 7.56 (s, br, 1H), 7.47 (s, br, 1H) 4.78 (s, 2H), 2.32 (s, 3H) ppm. IR (KBr): 2240, 1770, 1720 cm-1 ; MS (m/z) 276 (M+).

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