N-bromobutanimide → HCID 70395582, compound

HRID 1905006Notes

Reaction equation

HRID 1905006 reaction equation
[CH2:1]1[C@@H:3]2[C:4](=[O:22])[CH:5]=[C:6]3[C@:19]([CH3:20])([CH:2]12)[C@@H:18]1[C@H:9]([C@H:10]2[C@@:14]([CH2:16][CH2:17]1)([CH3:15])[C:13](=[O:21])[CH2:12][CH2:11]2)[CH2:8][CH2:7]3.[Br:23]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:23][C@H:7]1[C:6]2[C@:19]([CH3:20])([CH:2]3[CH2:1][C@@H:3]3[C:4](=[O:22])[CH:5]=2)[C@@H:18]2[C@H:9]([C@H:10]3[C@@:14]([CH2:16][CH2:17]2)([CH3:15])[C:13](=[O:21])[CH2:12][CH2:11]3)[CH2:8]1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 13564888HCID 13564888, compound

Product 1

HCID 70395582HCID 70395582, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 1,2β-methylenandrost-4-ene-3,17-dione (2.44 g), N-bromosuccinimide (2.33 g), benzoyl peroxide (0.060 g), and carbon tetrachloride (200 ml) are heated to reflux for 4 hours. After cooling to room temperature the precipitate is filtered off, the residue washed with carbon tetrachloride and the combined filtrates evaporated in vacuo. The residue is chromatographed on silica gel using benzene/ethyl ether to give pure 6β-bromo-1,2β-methylenandrost-4-ene-3,17-dione (2.16 g, 70%).

Workup

  1. temperatureare heated
  2. temperatureto reflux for 4 hours
  3. filtrationis filtered off
  4. washthe residue washed with carbon tetrachloride
  5. customthe combined filtrates evaporated in vacuo
  6. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-6b145830802d469d96c458fe111a1f04
Source dataset
uspto-grants-1989_06
Patent number
US04840943

Reaction notes

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