2-Hydroxydibenzofuran on bromination gives 1-bromo-2-hydroxydibenzofuran (m.p., 123.5°) and 2-hydroxy-3-bromo-dibenzofuran (m. p., 143-144°). The corresponding products but in a different ratio are obtained by the bromination of 2-methoxydibenzofuran. The allyl ether of 2-hydroxydibenzofuran rearranges to 1-allyl-2-hydroxydihenzofuran (m.p., 82.5°-83°), the methyl ether of which melts at 68°. Also, 2-hydrozydibenzofuran and benzenediazonium chloride couple to give l-phenylazo-2-hyclroxydibenzofuran. The 3-hydroxydibenzofuran couples to give 2-phenylazo-3- hydroxydibenzofuran (m. p., 166°), the structure of which was established by conversion to 2-bromo-3-hydroxydibenzofuran (m.p., 166°), the structure of which was established by conversion to 2-bromo-3-hydroxydibenzofuran (m.p., 115°-116°).
Proceedings of the Iowa Academy of Science
©1936 Iowa Academy of Science, Inc.
Jacoby, A. L.; Hayes, D. M.; and Ess, P.R. Van
"Orientation Studies in the Dibenzofuran Series,"
Proceedings of the Iowa Academy of Science, 43(1), 204-205.
Available at: https://scholarworks.uni.edu/pias/vol43/iss1/48