An oxidation of benzyl methyl ethers with nbs that selectively affords either aromatic aldehydes or aromatic methyl esters.
Either mono- or dibromination of benzyl methyl ethers can be achieved by controlling the amount of NBS and the temperature. Elimination of methyl bromide from the monobrominated intermediates produces aromatic aldehydes, whereas hydrolysis of the dibrominated intermediates affords aromatic methyl esters in good yields.
Mayhoub
Abdelrahman S
AS
Department of Medicinal Chemistry and Molecular Pharmacology, School of Pharmacy and Pharmaceutical Sciences, and the Purdue Center for Cancer Research, Purdue University, West Lafayette, Indiana 47907.
Talukdar
Arindam
A
Cushman
Mark
M
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D001555:Benzene Derivatives / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D006841:Hydrocarbons, Aromatic / Q000138:chemical synthesis* / Q000737:chemistry; D008738:Methyl Ethers / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D013388:Succinimides / Q000737:chemistry*
D000447:Aldehydes; D001555:Benzene Derivatives; D004952:Esters; D006841:Hydrocarbons, Aromatic; D008738:Methyl Ethers; D013388:Succinimides