The bromination of camphor has been carried out on a multi-gram scale by a mixture of KBr and KBrO 3 in the presence of acid or with HBr/NaBr -H + and H 2 O 2 /oxone ® as the oxidant. The 3-bromocamphor is then efficiently converted to camphorquinone by an improved oxidation protocol using DMSO and sodium carbonate of tetrabutyl ammonium iodide.
The asymmetric unit of the title hemisolvate, C28H39N3O4·0.5CH2Cl2 contains two isophthalamide camphor derivatives and one dichloromethane solvent molecule. In the crystal, the chiral molecules are connected into [100] stacks by N—H...O and C—H...O hydrogen bonds. The stacks are consolidated by C—H...N and C—H...Cl as well as further C—H...O interactions.
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