Halogenated cinnamic acids and esters thereof, processes for the

Details Halogenated cinnamic acids and esters thereof, processes for the Halogenated cinnamic acids and esters thereof, processes for the

1994-01-06

1996-05-14

Killos, Paul J.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acid esters

562495, 562443, 562470, 560 38, 560 60, C07C 6976

Patent

active

055169325

ABSTRACT:
The present invention relates to compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 are identical or different and are hydrogen or an alkyl radical having 1 to 18 carbon atoms and optionally containing oxygen, nitrogen or halogen, the radicals X, Y and Z are identical and are a fluorine, bromine or iodine atom or if two of the radicals X, Y or Z are identical or all of the radicals X, Y, Z are different from each other, X, Y and Z are a fluorine, chlorine, bromine or iodine atom. The invention further relates to a process for the preparation of the compounds, by reacting an aryldiazonium salt of the formula ##STR2## in which the radicals X, Y and Z are identical and are a fluorine, bromine or iodine atom or, if two of the radicals X, Y and Z are identical or all of the radicals X, Y, Z are different from each other, X, Y and Z are a fluorine, chlorine, bromine or iodine atom and A.sup.(-) is an anion of an acid having a pK.sub.a <7, with a compound of the formula ##STR3## in which R.sup.1 and R.sup.2 are identical or different and are hydrogen or an alkyl radical having 1 to 18 carbon atoms and optionally containing oxygen, nitrogen or halogen, in the presence of a palladium-containing catalyst, if appropriate with addition of a base, and the aryldiazonium salts of the formula (II).

REFERENCES:
patent: 3345263 (1967-10-01), Subbaratnam
patent: 4346248 (1982-08-01), Deavenport et al.
patent: 5093515 (1992-03-01), Kumai et al.
CA. 108:108029 1988.
Chemical Abstracts, vol. 58, No. 3, 1963, abstract no. 2389g.
Chemical Abstracts, vol. 51, No. 12, 1957, abstract no. 8667a.
Chemical Abstracts, vol. 74, No. 25, 1971, abstract no. 139822r.
Chemical Abstracts, vol. 95, No. 5, 1981, abstract no. 42172m.
Tetrahedron, vol. 37, No. 1, 1981, pp. 31-36.

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