Pyridine → Carbonic acid chloromethyl ester 2,6-dibromo-4-cyanophenyl ester

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Reaction Steps

To a suspension of 3,5-dibromo-4-hydroxybenzonitrile (10.0 g, 36.1 mmol) in 180 mL of chloroform was added pyridine (2.92 ml, 36.1 mmol). Chloromethylchloroformate (5.2 mL 60 mmol) was then added over 5 min. The mixture was allowed to stir at room temperature for 12 h. The reaction was then washed with 1% HCl aq, water, and brine. The organic layer was then dried over sodium sulfate, filtered, and evaporated to afford a white solid (12.5 g) in 94% yield. 1H-NMR (300 MHz, CDCl3) δ (ppm): 5.87 (d, 2H), 7.90 (s, 2H). 13C-NMR (300 MHz, CDCl3) δ (ppm): 73.58, 113.87, 115.68, 119.01, 136.40, 149.53, 149.71. Mp=83-85° C.

Provenance & Evidence