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Citation: CAI Chao-Jun, HU Bing-Cheng, Lu Chun-Xu. Synthesis of 2-Ethoxycarbonyl-3-bromo-4-methyl-5-formyl-pyrrole[J]. Chinese Journal of Applied Chemistry, ;2006, 23(7): 798-802. shu

Synthesis of 2-Ethoxycarbonyl-3-bromo-4-methyl-5-formyl-pyrrole

1.
School of Chemical Engineering, Nanjing University of Science & Technology, Nanjing 210094

Corresponding author: HU Bing-Cheng,
Received Date: 12 August 2005
Available Online: 16 November 2005

2-Ethoxycarbonyl-4,5-dimethyl-pyrrole(7) was prepared from ethylacetoacetate,ethyl formate and methyl ethyl ketone via oximination,Claisen condensation,and reductive condensation.The bromization of compound 7 gave 2-ethoxycarbonyl-3-bromo-4,5-dimethyl-pyrrole(8),which could be transferred to 2-ethoxycarbonyl-3-brome-4-methyl-5-formyl-pyrrole(9) by the formolation.In the synthesis reaction of compound 7,its yield was maximum when pH,the mole ratio of zinc to compound 1 and reaction temperature were set as 3.8,2.8:1 and 90~95℃, respectively.The effects of solvent on the bromization reaction and oxidant on the formolation reaction of the target product were studied.The results show that the optimum solvent for the bromization reaction and the optimum oxidant for the formolation reaction of the target product were carbon tetrachloride and ceric ammonium nitrate,and their yields were 86.7% and 89.3% respectively.The structures of the compounds were characterized by elemental analysis,accurate mass,¹H NMR,IR and GC-MS.
- ethoxycarbonyldimethyl-pyrrole,
- ethoxycarbonylbromodimethyl-pyrrole,
- ethoxycarbonylbromemethylformyl-pyrrole
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