synthesis of 2-fluoromethyl-7-methylnaphthalene合成2-fluoromethyl-7-methylnaphthalene.pdfVIP

Molbank 2008, M568 OPEN ACCESS molbank ISSN 1422-8599 /molbank Short Note Synthesis of 2-Fluoromethyl-7-methylnaphthalene Jane Bogdanov *, † and Przemyslaw Maslak Department of Chemistry, The Pennsylvania State University, University Park, Pennsylvania 16802, USA. E-mail: nyl@ † Present address: Institute of Chemistry, Faculty of Natural Sciences Mathematics, Sts. Cyril and Methodius University, PO Box 162, 1000 Skopje, Macedonia *Author to whom correspondence should be addressed; Tel.: +389 2 324 9918; Fax: +389 2 3226865; E-mail: j_b_bogdanov@ Received: 31 July 2008 / Accepted: 18 August 2008 / Published: 22 August 2008 Keywords: Halogen exchange, nucleophilic fluorination, 2-fluoromethyl-7- methylnaphthalene 1. Introduction In connection with our investigation of competitive mesolytic cleavages [1] of radical anions we needed 2-fluoromethyl-7-methylnaphthalene, 2, as a gas chromatography standard. Our initial attempt was to prepare 2 via the corresponding known alcohol 2-hydroxymethyl-7-methylnaphthalene [2]. Treatment of the alcohol with the Olah’s reagent (HF/pyridine) [3], according to the procedure of Olah and co-workers for fluorination of alcohols [4] did not result in the desired fluoride. The alternative strategy was to employ halogen exchange using the bromo derivative 1 with a proper source of nucleophilic fluoride. The choice of fluoride source was cesium fluoride, which has appreciable solubility in polar aprotic organic solvents [5], especially when