Add time:08/24/2019 Source:sciencedirect.com
Substituted heterocycles, such as pyrrole and thiophene, are commonly found in the field of pharmaceutical and material sciences. Here we studied the reactivity of 4,5-unsubstituted alkyl 3-hydroxypyrrol-2-yl-carboxylates and 4,5-unsubstituted alkyl 3-hydroxythiophen-2-yl-carboxylates in different halogenation conditions, due to their interest as building blocks in the synthesis of bioactive compounds and materials. We describe herein the regioselective monohalogenation of 3-hydroxypyrroles and 3-hydroxythiophenes in mild conditions with common halogenation agents. The selectivity of the halogenation was studied. Optimized one-step reaction conditions were found for monobromination and monochlorination. Finally, we observed that bromination with N-bromosuccinimide (NBS) took place at the C4 position of the heterocycle, while chlorination with SO2Cl2 led to C5-halogenated derivatives.
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