1,3-Dibromo-5,5-dimethylhydantoin → 11beta-Fluoroestra-4,6-diene-3,17-dione

HRID 650345Notes

Reaction equation

HRID 650345 reaction equation
C([O-])(=O)C.[Na+].BrN1C(C)(C)C(=O)N(Br)C1=O.[F:17][C@H:18]1[CH2:35][C@@:33]2([CH3:34])[C@@H:29]([CH2:30][CH2:31][C:32]2=[O:36])[C@H:28]2[C@H:19]1[C@@H:20]1[C:25](=[CH:26][CH2:27]2)[CH:24]=[C:23]([O:37]C)[CH2:22][CH2:21]1.S([O-])([O-])=O.[Na+].[Na+].[Br-].[Li+].C(=O)([O-])[O-].[Li+].[Li+]>CN(C=O)C.C(OCC)(=O)C>[F:17][C@H:18]1[CH2:35][C@@:33]2([CH3:34])[C@@H:29]([CH2:30][CH2:31][C:32]2=[O:36])[C@H:28]2[C@H:19]1[C@@H:20]1[C:25]([CH:26]=[CH:27]2)=[CH:24][C:23](=[O:37])[CH2:22][CH2:21]1

Participants

9

Reactant 6

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 11125Lithium CarbonateHCID 24437Sodium SulfiteHCID 82050Lithium BromideHCID 517045Sodium AcetateHCID 1173826011beta-Fluoro-3-methoxyoestra-3,5-dien-17-one

Product 1

HCID 1117374411beta-Fluoroestra-4,6-diene-3,17-dione

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5 ml of a 10% sodium acetate solution and, in portions, 2.5 g of 1,3-dibromo-5,5-dimethylhydantoin are added in succession to 5.0 g of 11β-fluoro-3-methoxy-estra-3,5-dien-17-one in 50 ml of DMF at 20° C. After 30 minutes, 2.3 g of sodium sulfite is added and then 2.5 g of lithium bromide and 2.0 g of lithium carbonate, and it is stirred for 2 hours at 100° C. The reaction mixture is stirred into ice water. The precipitated product is suctioned off, dissolved in ethyl acetate, washed with water, dried and concentrated by evaporation in a vacuum. After recrystallization from ethyl acetate, 3.6 g of 11β-fluoro-estra-4,6-diene-3,17-dione with a melting point of 198° C. is obtained.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated by evaporation in a vacuum
  4. customAfter recrystallization from ethyl acetate, 3.6 g of 11β-fluoro-estra-4,6-diene-3,17-dione with a melting point of 198° C.
  5. customis obtained

Sources & evidence

ORD record
ord-244e817e913147f59984aee1a078eb9a
Source dataset
uspto-grants-2001_08
Patent number
US06271403B1

Reaction notes

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