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Process for the preparation of insecticidal, nematicidal and acaricidal 2-halo-3-substituted-5-arylpyrrole compounds
| Details |
Inventors: Lowen, Gregory T.;
Assignee: American Cyanamid Company (Stamford, CT)
Primary Examiner: Brust; Joseph Paul
Assistant Examiner: McKane; Joseph K.
Attorney, Agent or Firm: Brennan; Alice C.
There is provided a process for the preparation of 2-halo-3-substituted-5-arylpyrrole compounds which are useful as insecticidal, nematicidal and acaricidal agents. |
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DETAILED DESCRIPTION OF THE INVENTION One of the preferred embodiments of the present invention involves reacting a formula II substituted acetonitrile compound as described above with at least about 1 molar equivalent, preferably about 1 to 3 molar equivalents, of a base and at least about 1 molar equivalent, preferably about 1 to 3 molar equivalents, of a formula III substituted phenacyl halide compound as described above in the presence of a solvent preferably at a temperature range of about -5.
degree.
C.
to 40.
degree.
C.
to form a formula IV substituted phenacylacetonitrile compound as described above and reacting the formula IV compound in a solvent saturated with an excess of a hydrogen halide preferably hydrogen chloride or hydrogen bromide at a temperature range of about 0.
degree.
C.
to 50.
degree.
C.
to form 2-halo-3-substituted-5-arylpyrrole compounds of formula I.
The formula I compounds may be isolated by conventional techniques such as dilution of the reaction mixture with water and filtration or, alternatively, extraction with a suitable solvent.
Suitable extraction solvents include water-immiscible solvents such as ether, ethyl acetate, toluene, methylene chloride and the like.
Bases suitable for use in the process of the present invention include alkali metal C.
sub.
1 -C.
sub.
6 alkoxides, alkali metal hydroxides, alkali metal hydrides, alkali metal carbonates, C.
sub.
1 -C.
sub.
4 trialkylamines and pyridine.
Preferred bases are potassium tert-butoxide, sodium methoxide and sodium hydride.
Reaction solvents suitable for use in the present invention include organic solvents such as ether, tetrahydrofuran, chlorinated hydrocarbons, C.
sub.
1 -C.
sub.
6 alcohols and mixtures thereof.
Chlorinated hydrocarbons and tetrahydrofuran are preferred reaction solvents.
Formula II substituted acetonitriles are prepared according to the procedures of A.
R.
Surrey, Journal of the American Chemical Society, 65, pages 2471-2472, 1943; F.
B.
Thole et al.
, Journal of the Chemical Society, 99, pages 422-448, 1911; P
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Molecular Biology 
