Process for the preparation of 2-(2',2',2'-trihalogenoethyl)-4-h

Details Process for the preparation of 2-(2',2',2'-trihalogenoethyl)-4-h Process for the preparation of 2-(2',2',2'-trihalogenoethyl)-4-h

1978-10-03

1980-12-30

Trousof, Natalie

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

Organic compounds

Oxygen containing

568364, 568367, 560118, 560124, 562500, 562506, 568381, C07C 4545, C07C 49105, C07C 49115

Patent

active

042422787

ABSTRACT:
A process for the preparation of 2-(2',2',2',-trihalogenoethyl)-4-halogenocyclobutan-1-ones of the formula ##STR1## in which one of the radicals R.sub.1 and R.sub.2 is methyl and the other is hydrogen or methyl, or R.sub.1 and R.sub.2 together are an alkylene group having 2 to 4 carbon atoms, and X and Y are each chlorine or bromine, comprising reacting a 2,4,4,4-tetrahalogenobutyric acid chloride in the presence of an organic base with an ethylene compound which is disubstituted in 1-position by the radicals R.sub.1 and R.sub.2, as defined above, to form a 2-(2',2',2'-trihalogenoethyl)-2-halogenocyclobutan-1-one and then rearranging the latter, in the presence of a catalyst, into a 2-(2',2',2'-trihalogenoethyl)-4-halogenocyclobutan-1-one of the above formula; said 2-(2',2',2'-trihalogenoethyl)-4-halogenocyclobutan-1-ones being valuable intermediates for the preparation of 2-(2',2'-dihalogenovinyl)-cyclopropanecarboxylic acid and its insecticidally active esters; as well as the 2-(2',2',2'-trihalogenoethyl)-4-halogenocyclobutan-1-ones of the above formula and the intermediates utilized for their preparation.

REFERENCES:
patent: 3642904 (1972-02-01), Langkammerer
patent: 3655765 (1972-04-01), Gelfand
patent: 4028418 (1977-06-01), van den Brink et al.
patent: 4064174 (1977-12-01), Verbrugge
J. Am. Chem. Soc., 87, 5257, (1965).
Tetrahedron Letters, No. 1, 135-139, (1966).

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