doi: 10.1021/jo1004313.
An oxidation of benzyl methyl ethers with nbs that selectively affords either aromatic aldehydes or aromatic methyl esters
Affiliations
- PMID: 20373742
- PMCID: PMC2871065
- DOI: 10.1021/jo1004313
Item in Clipboard
An oxidation of benzyl methyl ethers with nbs that selectively affords either aromatic aldehydes or aromatic methyl esters
J Org Chem.
.
Abstract
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.
Figures
Postulated Reaction Pathways
Benzyl Methyl Ether Oxidation Reactions
Thiazolyl Methyl Ether Oxidation Reactions
Conversion of 1e to 3e.
Similar articles
-
Bu4NI-catalyzed benzylic acyloxylation of alkylarenes with aromatic aldehydes.Chem Commun (Camb). 2012 Oct 21;48(82):10204-6. doi: 10.1039/c2cc35450k. Chem Commun (Camb). 2012. PMID: 22968182
-
Site-selective electrooxidation of methylarenes to aromatic acetals.Nat Commun. 2020 Jun 1;11(1):2706. doi: 10.1038/s41467-020-16519-8. Nat Commun. 2020. PMID: 32483217 Free PMC article.
-
Synthesis of Chiral, Enantiopure Allylic Amines by the Julia Olefination of α-Amino Esters.Molecules. 2016 Jun 21;21(6):805. doi: 10.3390/molecules21060805. Molecules. 2016. PMID: 27338326 Free PMC article.
-
Oxidation using activated carbon and molecular oxygen system.Chem Rec. 2008;8(4):252-67. doi: 10.1002/tcr.20152. Chem Rec. 2008. PMID: 18752318 Review.
-
Use of solid catalysts in Friedel-Crafts acylation reactions.Chem Rev. 2006 Mar;106(3):1077-104. doi: 10.1021/cr040695c. Chem Rev. 2006. PMID: 16522017 Review. No abstract available.
Cited by
-
SAR Studies of the Leupyrrins: Design and Total Synthesis of Highly Potent Simplified Leupylogs.Chemistry. 2020 Nov 26;26(66):15074-15078. doi: 10.1002/chem.202002622. Epub 2020 Oct 15. Chemistry. 2020. PMID: 32608026 Free PMC article.
-
Regioselective α-Amination of Ethers Using Stable N-Chloroimides and Lithium tert-Butoxide.J Org Chem. 2019 Jul 5;84(13):8710-8716. doi: 10.1021/acs.joc.9b00824. Epub 2019 Jun 19. J Org Chem. 2019. PMID: 31244155 Free PMC article.
-
Recent Progress on Photocatalytic Synthesis of Ester Derivatives and Reaction Mechanisms.Top Curr Chem (Cham). 2021 Oct 19;379(6):42. doi: 10.1007/s41061-021-00355-5. Top Curr Chem (Cham). 2021. PMID: 34668085 Review.
-
Stereospecific Radical Bromination of β-Aryl Alcohols with Thiourea Additives Through A Serendipitous Discovery of A 1,2-Aryl Migration.Chemistry. 2025 Apr 1;31(19):e202403831. doi: 10.1002/chem.202403831. Epub 2025 Jan 15. Chemistry. 2025. PMID: 39745478 Free PMC article.
-
Oxidation of Secondary Methyl Ethers to Ketones.J Org Chem. 2017 Jul 7;82(13):6671-6679. doi: 10.1021/acs.joc.7b00632. Epub 2017 Jun 12. J Org Chem. 2017. PMID: 28585818 Free PMC article.
References
-
- Feltenberger JB, Hayashi R, Tang Y, Babiash ESC, Hsung RP. Org. Lett. 2009;11:3666. - PMC - PubMed
- Rayabarapu DK, Zhou A, Jeon KO, Samarakoon T, Rolfe A, Siddiqui H, Hanson PR. Tetrahedron. 2009;65:3180. - PMC - PubMed
- Batsomboon P, Phakhodee W, Ruchirawat S, Ploypradith P. J. Org. Chem. 2009;74:4009. - PubMed
-
- Chen Y, Cho C, Larock RC. Org. Lett. 2009;11:173. - PMC - PubMed
- Martinez C, Alvarez R, Aurrecoechea JM. Org. Lett. 2009;11:1083. - PubMed
- Iwai T, Fujihara T, Terao J, Tsuji Y. J. Am. Chem. Soc. 2009;131:6668. - PubMed
- Mahboobi S, Dove S, Sellmer A, Winkler M, Eichhorn E, Pongratz H, Ciossek T, Baer T, Maier T, Beckers T. J. Med. Chem. 2009;52:2265. - PubMed
-
- Markees DG. J. Org. Chem. 1958;23:1490.
-
- Lovins RE, Andrews LJ, Keef RM. J. Org. Chem. 1963;28:2847.
-
- Micheal EM, Hangenah JA. Heterocycles. 1987;25:117.
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources
Other Literature Sources
Research Materials
Miscellaneous
