Selective preparation of α,α-dichloroketones with copper(II) chloride

Synthetic Communications

Volumn 32, Issue 24, 2002, Pages 3711-3717

  Nobrega, José Arimateia ^a   Gonçalves, Simone Maria C ^a   Peppe, Clovis ^b  

^a FEDERAL UNIVERSITY OF PERNAMBUCO   (Brazil)

^b FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

Copper(II) chloride; Dichlorination; Dichloroketones

Indexed keywords

ALPHA,ALPHA DICHLOROKETONE DERIVATIVE; COPPER CHLORIDE; HYDROCHLORIC ACID; KETONE DERIVATIVE; N,N DIMETHYLFORMAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; CHLORINATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0036937495     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120015383     Document Type: Article

References (13)

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7. Larock, R.C. Comprehensive Organic Transformations; VCH Publishers: New York, 1989; 369-380.
8. Shi, X.X.; Dai, L.X. Mild halogenation of stabilized ester enolates by cupric halides. J. Org. Chem. 1993, 58, 4596-4598.
9. Kosower, E.M.; Cole, W.J.; Wu, G.S.; Cardy, D.E.; Meisters, G.J. Halogenation with copper(II). Saturated ketones and phenol. J. Org. Chem. 1963, 28, 630-633.
10. (a) King, L.C.; Ostrum, G.K. Selective bromination with copper(II) bromide. J. Org. Chem. 1964, 29, 3459-3461;
11. (b) Doifode, K.B.; Marathey, M.G. Reactions of cupric bromide in dioxane. Formation of ω-bromo-o-hydroxyacetophenone. J. Org. Chem. 1964, 29, 2025-2026.
12. 2: ketone of 6: 1.
13. The choice of DMF as the solvent was crucial. Reactions do not occur in acetonitrile and 1,4-dioxane.