Methyl iodide → 2-(4-Bromo-2,6-dimethylphenyl)-3-methoxy-cyclopent-2-enone

HRID 514190Notes

Reaction equation

HRID 514190 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]2[C:13](=[O:14])[CH2:12][CH2:11][C:10]2=[O:15])=[C:4]([CH3:16])[CH:3]=1.[C:17](=O)([O-])[O-].[K+].[K+].IC>CC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]([CH3:16])[C:5]([C:9]2[C:13](=[O:14])[CH2:12][CH2:11][C:10]=2[O:15][CH3:17])=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 896009062-(4-Bromo-2,6-dimethylphenyl)cyclopentane-1,3-dione

Product 1

HCID 668681542-(4-Bromo-2,6-dimethylphenyl)-3-methoxy-cyclopent-2-enone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
27.5 °C

Procedure

To a solution of 2-(4-bromo-2,6-dimethylphenyl)cyclopentane-1,3-dione (40 g, 0.143 mol) in acetone (2000 ml) is added anhydrous potassium carbonate (98.5 g, 0.714 mol) and iodomethane (45 ml, 0.72 mol). The resulting mixture is stirred at 25-30°C. for 16 hours, then volatile solvents are removed in vacuo, and the residue is diluted with distilled water (200 ml) and extracted with ethyl acetate (3×500 ml). Organic fractions are combined, washed with distilled water, brine, then dried over sodium sulphate, filtered and the filtrate concentrated in vacuo. The crude product is purified by flash column chromatography to afford 2-(4-bromo-2,6-dimethylphenyl)-3-methoxycyclopent-2-enone.

Workup

  1. customvolatile solvents are removed in vacuo
  2. additionthe residue is diluted with distilled water (200 ml)
  3. extractionextracted with ethyl acetate (3×500 ml)
  4. washwashed with distilled water, brine
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated in vacuo
  8. customThe crude product is purified by flash column chromatography

Sources & evidence

ORD record
ord-2f1be38455e648869d39927cce4df506
Source dataset
uspto-grants-2015_08
Patent number
US09107415B2

Reaction notes

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