Facile nucleophilic fluorination of primary alkyl halides using tetrabutylammonium fluoride in a tert-alcohol medium

✍ Scribed by Dong Wook Kim; Hwan-Jeong Jeong; Seok Tae Lim; Myung-Hee Sohn

• Book ID: 104097162
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 238 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2009.11.058

✦ Synopsis

Nonpolar protic reaction media such as t-amyl alcohol allow the aliphatic, nucleophilic fluorination reaction of primary haloalkane systems to fluoroalkanes, using tetrabutylammonium fluoride (TBAF), to proceed chemo-selectively at a reasonable reaction rate under mild conditions to afford the fluoro-product in high yield. As an example, the nucleophilic fluorination of 2-(3-iodopropoxy)naphthalene (1a) as the primary haloalkane model compound, with TBAF in acetonitrile as a polar aprotic solvent, CsF in t-amyl alcohol as a nonpolar protic solvent, and TBAF in t-amyl alcohol for 1 h provided 2-(3-fluoropropoxy)naphthalene (2a) in 38, 5 and 76% yields, respectively.