2-(5-Bromo-2-ethylphenyl)cyclopent-4-ene-1,3-dione → 2-(5-Bromo-2-ethylphenyl)cyclopentane-1,3-dione

HRID 339468Notes

Reaction equation

HRID 339468 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:15][CH3:16])=[C:6]([CH:8]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]2=[O:14])[CH:7]=1>C(O)(=O)C.[Zn]>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:15][CH3:16])=[C:6]([CH:8]2[C:12](=[O:13])[CH2:11][CH2:10][C:9]2=[O:14])[CH:7]=1

Participants

4

Reactant 1

HCID 580614862-(5-Bromo-2-ethylphenyl)cyclopent-4-ene-1,3-dione

Product 1

HCID 666773502-(5-Bromo-2-ethylphenyl)cyclopentane-1,3-dione

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Procedure

To a suspension of zinc dust (13.9 g, 214 mmol) in acetic acid (270 ml) is added a solution of 2-(5-bromo-2-ethylphenyl)cyclopent-4-ene-1,3-dione (8.544 g, 31 mmol) in acetic acid (70 ml). The reaction mixture is stirred at room temperature for 18 hours, then filtered through diatomaceous earth and washed with acetic acid and concentrated under reduced pressure. The crude oil is azeotroped with toluene (×2) then concentrated in vacuo and purified by flash column chromatography on silica gel to afford 2-(5-bromo-2-ethylphenyl)cyclopentane-1,3-dione.

Workup

  1. filtrationfiltered through diatomaceous earth
  2. washwashed with acetic acid
  3. concentrationconcentrated under reduced pressure
  4. customThe crude oil is azeotroped with toluene (×2)
  5. concentrationthen concentrated in vacuo
  6. custompurified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-434b80d936c64744bbf26aa95835f325
Source dataset
uspto-grants-2014_11
Patent number
US08895474B2

Reaction notes

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