Preparation of fluorine-containing phenylacetylenes by the method of introduction of the ethynyl group using 1,1-dichloro-2,2-difluoroethene.

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概要

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• Phenylacetylenes (ArC≡CH) having fluoro- or trifluoromethyl substituents (<I>o</I>-, <I>m</I>-, <I>p</I>-F; <I>o</I>-, <I>m</I>-, <I>p</I>-CF<SUB>3</SUB>; 2,4-, 2,5-, 2,6-, 3,5-(CF<SUB>3</SUB>)<SUB>2</SUB>) have been prepared from bromobenzenes (ArBr) and benzenes (ArH) using 1,1-dichloro-2,2-difluoroethene (<B>1</B>) by a two-step route: ArLi or ArMgBr→ArCF=CCl<SUB>2</SUB>→ArC≡CLi. Upon careful treatment at −70 °C with <B>1</B>, <I>o</I>-fluorophenyllithium gave <I>o</I>-FC<SUB>6</SUB>H<SUB>4</SUB>CF=CCl<SUB>2</SUB> in good yield, together with benzyne-derived products, such as <I>o</I>-(<I>o</I>-FC<SUB>6</SUB>H<SUB>4</SUB>)C<SUB>6</SUB>H<SUB>4</SUB>CF=CCl<SUB>2</SUB>. Lithiation of <I>m</I>-bis(trifluoromethyl)benzene at 0 °C for 9 h (24 h) followed by treatment with bromine gave 1-bromo-2,4-, 2,6-, and 3,5-bis(trifluoromethyl)benzene in 35 (38), 31 (36), and 8% (6%) yield, respectively.

• 公益社団法人 日本化学会の論文

著者

• Kodaira Kazuo

  Government Industrial Research Institute

• Okuhara Kunio

  Government Industrial Research Institute

関連論文

• The electrochemical fluorination of trifluoromethyl-substituted benzenes.
• Electrochemical fluorination of ethanethiol.
• The Fluorination of Carbon Monoxide, Carbonyl Chloride, and Carbonyl Fluoride
• The Fluorination of Carbonyl Sulfide
• Electrochemical fluorination of thiols.
• Chlorofluorination of Carbon Disulfide and Sulfur
• The Electrochemical Fluorination of s-Triazines
• Acetylenic and polyacetylenic compounds derived from thiophene, furan, and p-dibromobenzene using 1,1-dichloro-2,2-difluoroethene.
• The Electrochemical Fluorination of Benzenes and Pyridines
• Preparation of fluorine-containing phenylacetylenes by the method of introduction of the ethynyl group using 1,1-dichloro-2,2-difluoroethene.

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