Abstract
The reaction of thiophene and dichlorodifluorobenzyne generated by lithiation of sym-trichlorotrifluorobenzene in diethyl ether-hexane solution at room temperature gave 1, 3-dichloro-2, 4-difluoronaphthalene [4] and 3, 5-dichloro-2, 4, 6-trifluorothiophenol in 39 and 22% yield, respectively. The thiophenol was also obtained in good yield from 3, 5-dichloro-2, 4, 6-trifluorolithiobenzene and sulfur.Lithiation of [4] gave 3-lithio compound exclusively and 1-chloro-2, 4-difluoronaphthalene and 4-chloro-1, 3-difluoro-2-naphthoic acid were obtained by hydrolyzation or carboxylation of the lithio compound.Equimolecular amount of potassiun hydroxide in methanol replaced one chlorine atom of [4] yielding a mixture of chlorodifluoromethoxynaphthalenes and the both chlorine atoms were methoxylated when excess alkali was used.2, 4, 6-Trichloro-3, 5-difluoroanisole was lithiated at the 4-position and 3, 5- dichloro-2, 6-difluoro-4-methoxybenzoic acid, 3, 5-dichloro-2, 6-difluoro-4-methoxythiophenol and 1, 3-dichloro-4-fluoro-2-methoxynaphthalene were prepared by reaction of the lithio compound with carbon dioxide, sulfur or thiophen, respectively.
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