184473-59-4Relevant articles and documents
One-pot Claisen rearrangement/O-methylation/alkene isomerization in the synthesis of ortho-methoxylated phenylisopropylamines
Waldman, Steve R.,Monte, Aaron P.,Bracey, Ann,Nichols, David E.
, p. 7889 - 7892 (1996)
An improved synthesis of a potent serotonin agonist 1a and its novel derivative 1b is described, making use of a Claisen rearrangement whose unstable phenolic product is methylated and isomerized in situ. This method may be of general use in the synthesis of α-methoxylated phenethylamine derivatives. The synthesis also includes an unusual, one pot demethylation/primary alcohol bromination with boron tribromide.