synthesis of 2,7-bis(fluoromethyl)naphthalene合成2,7-bis(fluoromethyl)萘.pdfVIP

Molbank 2008, M567 OPEN ACCESS molbank ISSN 1422-8599 /molbank Short Note Synthesis of 2,7-Bis(fluoromethyl)naphthalene 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: 19 August 2008 / Published: 22 August 2008 Keywords: Halogen exchange, nucleophilic fluorination, 2,7- bis(fluoromethyl)naphthalene 1. Introduction In connection with our investigation of the competitive mesolytic cleavages [1] of radical anions we have prepared several symmetrically substituted 2,7-bis(halomethyl)naphthalene derivatives. The starting material for these derivatives was 2,7-bis(bromomethyl)naphthalene 1, which could be conveniently obtained by benzylic bromination of the commercially available 2,7-dimethylnaphthalene using the procedure described by Reid and co-workers [2]. Our inital attempts of preparing 2,7- bis(fluoromethyl)naphathalene by treatment of the known 2,7-bis(hydroxymethyl)naphthalene [3] with Olah’s HF/pyridine reagent [4,5] met with failure. The alternative strategy was to employ halogen exchange using the bromo derivative 1 with a prope