Catalytic fluorination of dichloromethylbenzene by HF in liquid phase. Preparation of fluorinated building blocks

• Published in: Journal of fluorine chemistry Vol. 134; pp. 103 - 106
• Main Authors: Piou, Alexandre, Celerier, Stephane, Brunet, Sylvette
• Format: Journal Article
• Language: English
• Published: Elsevier B.V 01.02.2012; Elsevier
• Subjects: Antimony; Antimony trifluoride; Catalysis; Catalysts; Chemical Sciences; Dichloromethylbenzene; Dioxane; Exchange; Fluorination; Hafnium; Lewis acid; Pyridine; Pyridines; Solvents; Tributylphosphate; Lewis acid; Dichloromethylbenzene; Dioxane; Pyridine; Tributylphosphate; Antimony trifluoride; Fluorination; HF
• ISSN: 0022-1139; 1873-3328
• DOI: 10.1016/j.jfluchem.2011.04.003

The selective fluorination by successive Cl/F exchanges of the dichloromethylbenzene, was studied in the presence of HF as the fluorinating agent. The influence of the presence of a catalyst or a basic solvent (such as dioxane, pyridine, tributylphosphate) in order to favour the fluorination was investigated. [Display omitted] ► Two reaction in competition for the transformation of the dichloromethylbenzene. ► Fluorination reaction favored in the presence of HF-base system. ► Increase of the fluorination in the presence of the catalytic system HF-base-SbF 3. The selective fluorination by successive Cl/F exchanges of the dichloromethylbenzene, was studied in the presence of HF as the fluorinating agent. The influence of the presence of a catalyst or a basic solvent (such as dioxane, pyridine, tributylphosphate) in order to favour the fluorination was investigated. In mild conditions, (50 °C and after 1 h of reaction), the fluorination of the dichloromethylbenzene was observed and the polymerization reaction inhibited. The best results were obtained in the presence of the HF-dioxane system and antimony trifluoride as catalyst.