Experientia

, Volume 3, Issue 3, pp 107–107 | Cite as

The bromination of saturated 3-ketosteroids with N-bromo-imides

  • Carl Djerassi
  • Caesar R. Scholz
Kurze Mitteilungen

Zusammenfassung

Die Bromierung von gesättigten 3-Keto-steroiden mit N-Brom-succinimid oder N-Brom-phthalimid liefert die 2-Brom-3-keto-steroide bei Verbindungen, die derallo-Reihe angehören, und die 4-Brom-3-keto-steroide bei Vertretern dernormal-Reihe. Die weitere Bromierung eines 2-Brom-3-ketons zum 2,2-Dibrom-3-keton ist möglich.

References

  1. 1.
    Buu-Hoï, Exper.2, 310 (1946).Google Scholar
  2. 2.
    Meystre andWettstein, Exper.2, 408 (1946).Google Scholar
  3. 3.
    Wohl, Ber.52, 51 (1919).Google Scholar
  4. 3a.
    Wohl andJaschinowski, ib.54, 476 (1921).Google Scholar
  5. 4.
    Schmid andKarrer, Helv. chim. acta22, 573 (1946).Google Scholar
  6. 5.
    Cf.:Butenandt andWolff, Ber.68, 2091 (1935).Google Scholar
  7. 6.
    Cf.:Miescher and co-workers, Helv. chim. acta28, 1252, 1497 (1945);ib. 29, 33, 627 (1946).Google Scholar
  8. 7.
    In the latter case the crude bromination product, which was difficult to purify, was dehydrobrominated with pyridine to give methyl Δ4-3-keto-12-hydroxycholenate, m. p. 145–147,5° C, [α]D23=+80.3° (acetone), max. at 242 mµ (logΣ-4.28 in ethanol), in ca. 30% overall yield.Riegel andMcIntosh, J. amer. chem. Soc.66, 1099 (1944) obtained this compound in 35% yield, m. p. 114–145°C by the conventional bromination method followed by treatment with pyridine.Burckhard andReichstein, Helv. chim. acta25, 821 (1942) reported m. p. 150–152° C, [α]D17=+80.9° (acetone).Google Scholar

Copyright information

© Birkhäuser Verlag 1947

Authors and Affiliations

  • Carl Djerassi
    • 1
  • Caesar R. Scholz
    • 1
  1. 1.Research Department, Division of ChemistryCiba Pharmaceutical Products, Inc.SummitU.S.A.

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