Synthesis of 1-haloestradiols

Chemistry of carbon compounds – Miscellaneous organic carbon compounds – C-metal

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C07J 100

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045841373

ABSTRACT:
Estrogens characterized by an aromatic ring of the formula ##STR1## are halogenated by electrophilic substitution of a halo atom at the 1-position of the aromatic ring after protection of the sensitive 3-hydroxyl substituent and amination at the 4-position. Preferred starting materials include estrones or derivatives thereof. The estrones are preferably reduced after masking and amination to form the corresponding estradiols, which are then halogenated, deaminated and deprotected to provide the novel 1-haloestradiols.

REFERENCES:
patent: 3264330 (1966-08-01), Moersch et al.
patent: 3371087 (1968-02-01), Beard
patent: 4340602 (1982-07-01), Brooks
Hylarides et al., "Steroids", Feb. 1984, vol. 43, No. 2, pp. 219-224.
Hylarides et al, Jour. Org. Chem. (1984) vol. 49 (15) pp. 2744-2745.
G. W. Moersch et al, "The Syntheses and Myotrophic Activity of 1-Halo-4-Methylestra-1,3,5(10)-Trienes", May 21, 1964, pp. 741-748, vol. 7.

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