HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 11beta-Fluoro-7alpha-(5-bromopentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 7alpha-(5-Bromopentyl)-11beta-fluoro-estr-4-ene-3,17-dione | HCID 15870662 | — |
| Catalyst | Copper bromide (CuBr2) | HCID 24611 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 11beta-Fluoro-7alpha-(5-bromopentyl)-3-hydroxy-estra-1,3,5(10)-trien-17-one | HCID 15870663 | — |
Reaction Steps
17.0 g of copper(II) bromide are added at 80° C. to 27.8 g of 7α-(5-bromopentyl)-11β-fluorooestr-4-ene-3,17-dione in 190 ml of acetonitrile. After 8 hours, the reaction mixture is stirred into water, extracted 3 times with ethyl acetate, washed twice with ammonium chloride, with sodium hydrogencarbonate and sodium chloride, dried and concentrated in vacuo. After chromatographing the crude product on silica gel using a hexane-ethyl acetate gradient, 20.4 g of 7α-(5-bromo-pentyl)-11β-fluoro-3-hydroxyestra-1,3,5(10)-trien-17-one are obtained as colourless crystals of melting point 178° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06677324B1 |
| Source dataset | uspto-grants-2004_01 |
| ORD ID | ord-b83a279b3c5b4f2ba9ca0ef4fbeeed66 |
| Source note | uspto-grants-2004_01 |