Citric Acid → HCID 22467651, compound

Participants

Reaction Steps

To a solution of 2-chloro-5-methylphenyl methyl ether (12.0 g, 76 mmol) dissolved in CCl4 (200 mL) was added NBS (215.0 g, 83.6 mmol) and AIBN (0.63 g, 3.8 mmol). The reaction mixture was placed in an oil bath at 85° C. and stirred for 2-4 h. The reaction was cooled to RT, filtered and the solid washed with CCl4. The filtrate was evaporated and the resulting solid was dissolved in DMF (200 mL) then potassium phthalimide (35.0 g, 192 mmol) was added. The reaction mixture was placed in an oil bath at 60° C. and stirred for 2 h. The reaction mixture was cooled to RT then 10% citric acid (200 mL) was added and the mixture was extracted with EtOAc (3×200 mL). The organic extracts were combined, washed with water (50 mL) and brine (50 mL), dried over Na2SO4, filtered and evaporated. Purification was accomplished by column chromatography (hexane/EtOAc) to afford the title compound (15.0 g, 65%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.78-7.88 (m, 4H), 7.30 (d, 1H), 7.09 (d, 1H), 6.81 (dd, 1H), 4.72 (s, 2H), 3.80 (s, 3H). MS: m/z 324.0 (M+23).

Provenance & Evidence