Efficient Synthesis of 2-(Trimethylsilyl)phenyl Trifluoromethanesulfonate: A Versatile Precursor to o-Benzyne

Efficient Synthesis of 2-(Trimethylsilyl)phenyl Trifluoromethanesulfonate: A Versatile Precursor to o-Benzyne

An efficient procedure for the gram-scale preparation of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate, a versatile precursor to o-benzyne, is presented. The three-step sequence utilizes phenol as the starting material, requires only one chromatographic purification, and ultimately delivers the...

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Veröffentlicht in:Journal of organic chemistry 2009-11, Vol.74 (22), p.8842-8843
Hauptverfasser: Bronner, Sarah M, Garg, Neil K
Format: Artikel
Sprache:eng
Schlagworte:
Chemistry
Exact sciences and technology
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
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Zusammenfassung:An efficient procedure for the gram-scale preparation of 2-(trimethylsilyl)phenyl trifluoromethanesulfonate, a versatile precursor to o-benzyne, is presented. The three-step sequence utilizes phenol as the starting material, requires only one chromatographic purification, and ultimately delivers the desired silyltriflate in 66% overall yield.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo9020166