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Synthesis 2015; 47(08): 1091-1100
DOI: 10.1055/s-0034-1379992
DOI: 10.1055/s-0034-1379992
paper
Proximity- and Chelation-Induced SNAr 1,4-Aromatic ortho-Substitution of ortho-Methoxyphenyl 2-Alkyl Ketones
Weitere Informationen
Publikationsverlauf
Received: 20. November 2014
Accepted after revision: 22. Dezember 2014
Publikationsdatum:
12. Februar 2015 (online)
![](https://www.thieme-connect.de/media/synthesis/201508/lookinside/thumbnails/ss-2014-m0711-op_10-1055_s-0034-1379992-1.jpg)
Abstract
The direct displacement of an o-methoxy group in o-methoxyaryl ketones with aryl, alkyl, and alkenyl Grignard reagents to provide a series of o-substituted ketones is described. Application of this reaction to the synthesis of a C-methyl analogue of a cyclooxygenase inhibitor is shown. The scope and limitations are discussed.
Key words
aromatic substitution - biaryls - Grignard reaction in aryl ketones - steric hindrance - transition-metal-free reactionsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379992.
- Supporting Information
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