Synthese du 5-bromomethyl- et du 5-chloromethyl-2-furannecarboxaldehyde

Article abstract of DOI:10.1016/0008-6215(89)80052-7

The action of hydrogen halides, sulfur and phosphorous 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.