Carles [Bull. Soc., Chim., 17, 14 (1872)] prepared a monoiodovanillin in 1872, but did not prove its structure. Tiemann and Haarmann [Ber., 7, 615 (1874)] obtained a monobromo derivative that was shown by Dakin [Am. Chem. J., 42, 473 (1909)] to have the halogen in position 5 (CHO = 1). Peratoner [ Gazz. Chim. Ital., 28 (1) 235 (1898)] reported a monochloro compound in which the halogen was not oriented, but which may be a 5-derivative. The only dihalogenated vanillin on record is a diiodo compound obtained by Carles, for which no melting point was given, no derivatives prepared, and in which the halogen atoms were not oriented.
Proceedings of the Iowa Academy of Science
©1927 Iowa Academy of Science, Inc.
Raiford, L. Chas. and Stoesser, W. C.
"New Halogenated Derivatives of Vanillin,"
Proceedings of the Iowa Academy of Science, 34(1), 219-220.
Available at: https://scholarworks.uni.edu/pias/vol34/iss1/48