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

HRID 1193045Notes

Reaction equation

HRID 1193045 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12](=[O:13])[CH:11]=[CH:10][C:9]2=[O:14])=[C:4]([CH2:15][CH3:16])[CH:3]=1>C(O)(=O)C.[Zn]>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12](=[O:13])[CH2:11][CH2:10][C:9]2=[O:14])=[C:4]([CH2:15][CH3:16])[CH:3]=1

Participants

4

Reactant 1

HCID 580708792-(4-Bromo-2-ethylphenyl)cyclopent-4-ene-1,3-dione

Product 1

HCID 667097952-(4-Bromo-2-ethylphenyl)cyclopentane-1,3-dione

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Procedure

To a suspension of zinc dust (2.0 g, 0.03 mol) in glacial acetic acid (30 ml) is added a solution of 2-(4-bromo-2-ethylphenyl)cyclopent-4-ene-1,3-dione (1.20 g, 0.0043 mol) in glacial acetic acid (20 ml) dropwise over 10 minutes. After stirring of the resultant suspension for 20 hours at room temperature the reaction mixture is filtered through diatomaceous earth and the filtrate is evaporated under reduced pressure to afford 2-(4-bromo-2-ethylphenyl)cyclopentane-1,3-dione as a pink solid.

Workup

  1. filtrationis filtered through diatomaceous earth
  2. customthe filtrate is evaporated under reduced pressure

Sources & evidence

ORD record
ord-153c6d57a56e4d81bd0cd2975ee594fb
Source dataset
uspto-grants-2014_03
Patent number
US08680339B2

Reaction notes

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