Abstract
Fluorochlorobromoacetic acid was sythesized in the sequence of four steps from 1,1,2-trifluoro-2-chloroethylene in an overall yield of approximately 25%. 1,1,2-Trifluoro-2-chloroethylene was first allowed to react with sodium methoxide to form 1,2-difluoro-1-chloro-2-methoxyethylene, which was then brominated with elemental bromine and the reaction product treated with concentrated sulfuric acid to give methyl fluorochlorobromoacetate. This compound was hydrolized with a diluted sodium hydroxide solution to fluorochlorobromoacetic acid.
Zusammenfassung
Fluorchlorbromessigsäure wurde aus 1,1,2-Trifluor-2-chlorethylen in vier Stufen mit einer Gesamtausbeute von ca. 25% hergestellt. 1,1,2-Trifluor-2-chlorethylen wurde zuerst mit Natriummethoxid zu 1,2-Difluor-1-chlor-2-methoxyethylen umgesetzt, das dann mit elementarem Brom bromiert wurde. Das Reaktionsprodukt daraus ergab nach Behandlung mit konzentrierter Schwefelsäure Methyl-fluorchlorbromacetat, das nach Hydrolyse mit verdünnter Natronlauge zur Zielverbindung führte.
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This paper is dedicated to Professor Karl Schlögl on the occasion of his 65th birthday with warmest personal wishes
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Doyle, T.R., Vogl, O. A facile synthesis of fluorochlorobromoacetic acid. Monatsh Chem 121, 31–43 (1990). https://doi.org/10.1007/BF00810292
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DOI: https://doi.org/10.1007/BF00810292