Fmc Corporation

David E Seelye

Ernest L Plummer

Benzofurans of the formula ##STR1## wherein R.sup.1 is hydrogen, nitro, amino, phthalimido or acetamido, R.sup.2 is at least one of halo, cyano, alkyl(C.sub.1 -C.sub.8), cycloalkyl(C.sub.3 -C.sub.8), hydroxy, alkoxy(C.sub.1 -C.sub.8), acyl(C.sub.1 -C.sub.8), acyloxy(C.sub.1 -C.sub.8), alkoxy(C.sub.1 -C.sub.8)carbonyl, alkoxy(C.sub.1 -C.sub.8)carbonylalkyl(C.sub.1 -C.sub.8), phenyl, phenyloxy, trifluoromethyl or dialkyl(C.sub.1 -C.sub.8)amino, m is 0-3, and at least one of the carbon atoms of the benzene ring of said benzofuran is substituted. The compounds are intermediates in the preparation of pyrazoline insecticides.

Tetrafluoro-2,3-dihydrobenzofurans

Tetrafluorobenzofurans of the formula ##STR1## are prepared by contacting, at elevated temperature in an aprotic solvent, an ether of the formula ##STR2## with a catalytic mixture of metallic cooper and a polydentate or other ligand, wherein R.sup.1 is hydrogen, nitro, amino, phthalimido or acetylimido, R.sup.2 is at least one of hydrogen, halo, cyano, alkyl, hydroxy, alkoxy, acyl, acyloxy, alkoxycarbonyl, alkoxycarbonylalkyl, phenyl, phenyloxy, trifluoromethyl or dialkylamino. The products are intermediates in the preparation of pyrazoline insecticides.

Process of preparation of tetrafluoro 2,3-dihydrobenzofurans

Improved yields of biaromatic compounds, e.g., unsymmetrical biphenyl compounds, result by incorporating metallic copper in a non-aqueous diazonium-type coupling reaction.

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David E Seelye