Phase transfer catalyzed halogenation of carbon acids

Details Phase transfer catalyzed halogenation of carbon acids Phase transfer catalyzed halogenation of carbon acids

1991-07-12

1992-08-11

Lone, Werren B.

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

Organic compounds

Halogen containing

554153, 558460, 560174, 564204, 564209, 568316, 568409, 568437, 568460, 570101, 570190, 570206, 570216, 570261, C07C 1700, C07C 1702, C07C 6960, C07C 300

Patent

active

051381079

ABSTRACT:
A process is disclosed for chlorinating, brominating and/or iodinating an organic substrate containing both a single acidic hydrogen atom and at least one electron withdrawing group attached to the same carbon atom. The process replaces the single acidic hydrogen with chlorine, bromine and/or iodine and involves reacting the substrate in solution with a halogenating agent (e.g., a perhalomethane wherein the halogen substituents are I, Br and/or Cl, a trihaloacetic acid ester wherein the halogen substituents are Br and/or Cl, or a perfluoroalkyl halide wherein the halide is I, Br and/or Cl) in the presence of (i) a phase transfer catalyst of the formula R.sup.1 R.sup.2 R.sup.3 R.sup.4 LJ where L is selected from the group consisting of phosphorus and nitrogen, where J is an inorganic anion other than fluoride, and where R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently chosen from the froup consisting of hydrocarbyl radicals containing from 1 to about 20 carbon atoms and (ii) a mild inorganic base which is insoluble in the reaction medium.

REFERENCES:
patent: 4740624 (1988-04-01), Kohler et al.
patent: 4806280 (1989-02-01), Mignani et al.
C. Y. Meyers et al., New Synthesis and Reactions of Organic Compounds: Reactions with Carbon Tetrachloride and Other Perhalomethanes in Powdered Potassium Hydroxide-t-Butyl Alcohol. pp. 197-278.
M. Makosza et al., ROCZ Chem. 43, pp. 671-676.
A. Jonczyk et al., J. Org. Chem., 44, pp. 1192-1194.
S. E. Lauritzen et al., Acta Chem Scan, B 35, 1981, pp. 263-268.
Y. Hori et al., Rikogakubu Shoho, 6, pp. 19-22.
Y. Hori et al., Chem. Lett., 1978, pp. 73-76.
W. P. Reeves et al., "The Phase Transfer Catalyzed Preparation of 2-Methyl-2-Tricholormethyl-3-Phenyloxirane" Synth Comm., 13(11), 945-950 (1983).
C. Y. Meyers et al. "Facile and Selective Chlorination-Cleavage of Some Cyclanones and Cyclanols with the CCl.sub.4 -KOH-t-BuOH Reagent. In Situ Conversion of Estrones and Estradiols into Dichlorodoisynolic Acids" I. Org. Chem., 43, 1985-1990.
C. R. Hauser et al., "Reactions of Alkali Diphenylmethides with Certain Polyhalides. Displacement on Halogen or Hydrogen", I. Org. Chem., 26, pp. 2627-2629 (1961).

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