Synthèse du 5-bromométhyl- et du 5-chlorométhyl-2-furannecarboxaldéhyde

Add time:08/02/2019    Source:sciencedirect.com

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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