Pyridine → alpha-Cyano-6-bromo-2,3-dimethoxycinnamic acid

참여 물질

반응 단계

A mixture of 6-bromo-2,3-dimethoxybenzaldehyde (48.4 g, 0.20 mole), NH4OAc (1.93 g, 0.025 mole), cyanoacetic acid (0.186 mole, 15.8 g), pyridine (42 mL), and benzene (193 mL) was stirred at reflux for 2 hours using a Dean-Stark trap for water removal. Upon cooling to room temperature a solid was filtered and washed with hexane. The solid was dissolved in 1N KOH, and was extracted with ether. The aqueous layer was acidified with 10% HCl and was extracted with CH2Cl2. The combined CH2Cl2 layers were washed with water, saturated aqueous NaCl, dried (MgSO4), filtered, and evaporated to yield 41.7 g yellow solid, (67%); mp 130°-2°; M+ 311.

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