title: Preparation of brominated 2-alkoxythiophenes via oxidation and etherification of 2-thienyltrifluoroborate salts.
abstract: The synthesis of ring brominated long-chain 2-alkoxythiophenes is reported, involving mild (Oxone) oxidation of readily prepared 2-thienyltrifluoroborate salts followed by Mitsunobu etherification. Both procedures are operationally straightforward and use inexpensive reagents. Using this approach, several novel mono- and dibrominated octyloxythiophenes with previously elusive substitution patterns were prepared. One such compound was elaborated to a novel 5-alkoxythieno[3,2-b]thiophene-2-carboxylate ester, marking the first synthetic entry into this family of compounds.
authors.affiliation: Department of Chemistry and Biochemistry, Kent State University, Kent, Ohio 44242, USA.
authors.forename: Jonathan I
authors.initials: JI
authors.lastname: Tietz
authors.forename: Alexander J
authors.initials: AJ
authors.lastname: Seed
authors.forename: Paul
authors.initials: P
authors.lastname: Sampson