0000000000505265
AUTHOR
Christoph Holst
ChemInform Abstract: An Efficient Synthesis of Rubin′s Aldehyde and Its Precursor 1,3,5-Tribromo-2,4,6-tris(dichloromethyl)benzene.
The title compound (IV) serves as precursor of hexaethynylbenzenes and other [6]star compounds.
An Efficient Synthesis of Rubin’s Aldehyde and its Precursor 1,3,5-Tribromo-2,4,6-tris(dichloromethyl)benzene
2,4,6-Tribromobenzene-1,3,5-tricarboxaldehyde (4) can be efficiently prepared in two reaction steps from 1,3,5-tribromobenzene. The intermediate 1,3,5-tribromo-2,4,6-tris(dichloromethyl)benzene (3) crystallizes from petroleum ether in its C3h structure. However, in CDCl3 solution it exists at room temperature in two isomeric forms: 3a (C3h) and 3b (Cs) (1:1.15).The intramolecular Br・・・Cldistances are much smaller than the sum of the van der Waals radii. Therefore, the exocyclic C-C bonds show a hindered rotation.