A-ring bromination of estradiol and 17. cap alpha. -ethynylestradiol with N-chlorosuccinimide and bromide ion. Possible evidence for hypobromite intermediates

Journal Article · Fri Jan 01 04:00:00 EST 1982 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00341a037· OSTI ID:5192085

Wilbur, D S; O'Brien, Jr, H A

A-ring radiobrominated estrogens may have applications in the detection and/or choice of therapy for some types of tumors. A preliminary evaluation of radiobrominated steroids can be obtained through competitive receptorbinding studies, using the stable brominated compounds. We, therefore, soght to obtain purified samples of two different estrogens brominated in the A ring. Although methods of brominating in the A ring of estrogens have been described in the literature, we chose to employ a method that would convert bromide ion directly to an electrophilic brominating agent in situ. Such a method could be used for subsequent radiobrominations of these compounds. Studies in this laboratory have demonstrated that mixing N-chlorosuccinimide (NCS) and bromide ion forms an electrophilic brominating species in situ. We now report on the bromination of estradiol 1 and 17..cap alpha..-ethynylestradiol 5 with this combination of reagents.

• Research Organization: Los Alamos National Lab., NM
• OSTI ID: 5192085
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 47:2; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400702* -- Radiochemistry & Nuclear Chemistry-- Properties of Radioactive Materials
550601 -- Medicine-- Unsealed Radionuclides in Diagnostics
62 RADIOLOGY AND NUCLEAR MEDICINE
BIOCHEMICAL REACTION KINETICS
BROMINATION
CHEMICAL REACTIONS
CHEMICAL SHIFT
DATA
ESTRADIOL
ESTRANES
ESTROGENS
EXPERIMENTAL DATA
HALOGENATION
HORMONES
HYDROGEN COMPOUNDS
HYDROXY COMPOUNDS
INFORMATION
INORGANIC ACIDS
INTERMEDIATE STRUCTURE
KINETICS
LABELLING
LEWIS ACIDS
NUMERICAL DATA
ORGANIC BROMINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
REACTION KINETICS
SPECTRA
STEREOCHEMISTRY
STEROID HORMONES
STEROIDS