Sodium Iodide → HCID 54070378, compound

HRID 1073701Notes

Reaction equation

HRID 1073701 reaction equation
[Br:1][CH:2]1[CH2:19][C@@:18]2([CH3:20])[C:5]([C:6](Br)([CH2:22]Br)[CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[O:21])=[CH:4][C:3]1=[O:25].[I-].[Na+]>CC(C)=O>[Br:1][CH:2]1[CH2:19][C@@:18]2([CH3:20])[C:5]([C:6](=[CH2:22])[CH2:7][C@@H:8]3[C@@H:17]2[CH2:16][CH2:15][C@@:13]2([CH3:14])[C@H:9]3[CH2:10][CH2:11][C:12]2=[O:21])=[CH:4][C:3]1=[O:25]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 18642033HCID 18642033, compound

Product 1

HCID 54070378HCID 54070378, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A 250 ml 3-necked round bottomed flask fitted with a condenser, a thermometer and a magnetic stirrer is charged with 2.68 g of 2,6-dibromo-6-bromomethylandrost-4-ene-3,17-dione, 100 ml of acetone and 5.99 g of sodium iodide. The resulting suspension in refluxed for 15 min, cooled to room temperature, filtered and evaporated in vacuo. The residue is taken up with 50 ml of chloroform,washed twice with a saturated sodium thiosulfate aqueous solution, twice with water and dried over anhydrous calcium chloride. Evaporation of the solvent in vacuo yields 1.86 g of the crude title compound which is directly used for the next step.

Workup

  1. customA 250 ml 3-necked round bottomed flask fitted with a condenser
  2. temperatureThe resulting suspension in refluxed for 15 min
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. dry with materialdried over anhydrous calcium chloride
  6. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-0b5d98d25dd54fb4a3655452aba8fd53
Source dataset
uspto-grants-1990_11
Patent number
US04970327

Reaction notes

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