Process for preparing haloketo acid derivatives

Details Process for preparing haloketo acid derivatives Process for preparing haloketo acid derivatives

1991-02-07

1993-04-13

Prescott, Arthur C.

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

Organic compounds

Carboxylic acid esters

562577, C07C 69675, C07C 5976

Patent

active

052024679

ABSTRACT:
Process for preparing haloketo acid derivatives [I]: ##STR1## wherein R is H or C.sub.1-6 alkyl, and X is chlorine or bromine, which comprises reacting .beta.-oxo-acid ester [II]: ##STR2## wherein R.sup.1 is C.sub.1-6 alkyl, R.sup.2 is C.sub.1-5 alkyl or OR.sup.3 (R.sup.3 is C.sub.1-6 alkyl), and X is the same as above, with nitrosating agent [IV]:

REFERENCES:
patent: 4334087 (1982-06-01), Baer et al.
W. Theilheimer: "Synthetic Methods of Organic Chemistry Vol. 4", 1966, S. Karger, Basel, CH, p. 158, reaction 448, IBID vol. 6, 1952, pp. 305-306, reaction 823, IBID vol. 7, 1953, p. 199, reaction 511, IBID vol. 20, 1966, p. 307, reaction 370.
Houben-Weyl: "Methoden der Organischen Chemie vol. VII/2a 4th edition" 1973, Georg Thieme Verlag, Stuttgart DE, p. 800, 1,4-7; p. 804, par. 1.
J. March: "Advanced Organic Chemistry 2nd edition" (1977), McGraw Hill Int'l, Auckland AU, p. 419, par. 3-p, 420, par. 1.
J. Chem. Soc., 107, Synthesis of .alpha.-Tetronic Acid, by Kletz and Lapworth, pp. 1254-1265.
Chemical Abstr., 1957, 3457 (abstract of Bull. soc. chim. France 1956, 1361-1363).
J. Org. Chem. vol. 37, No. 3, 1972, 505-506.
J. Org. Chem. vol. 36, No. 23, 1971, 3553-3560.
J. Med. Chem. 1987, 30, 1074-1090.

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