Abstract
The action of hydrogen halides, sulfur and phosphorus halides, and halotrimethylsilanes on 5-(hydroxymethyl)-2-furancarboxaldehyde ( 1) led to the corresponding 5-(chloromethyl)- ( 2) or 5-(bromomethyl)-2-furancarboxaldehyde ( 3). Thus, treatment of 1 in diethyl ether solution with gaseous dry hydrogen chloride under very mild experimental conditions led to high yields of 2. The selective and quantitative conversion of 1 into 3 was achieved with bromotrimethylsilane. In the same manner, chlorotrimethylsilane gave high yields of 2 from 1. The latter compound was obtained by acid-catalyzed dehydration of d-fructose in dimethyl sulfoxide, and then converted into 2 without prior purification.
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