2-(4-Bromo-2,6-dimethylphenyl)cyclopent-4-ene-1,3-dione → 2-(4-Bromo-2,6-dimethylphenyl)cyclopentane-1,3-dione
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]2[C:13](=[O:14])[CH:12]=[CH:11][C:10]2=[O:15])=[C:4]([CH3:16])[CH:3]=1>C(O)(=O)C.[Zn]>[Br:1][C:2]1[CH:3]=[C:4]([CH3:16])[C:5]([CH:9]2[C:13](=[O:14])[CH2:12][CH2:11][C:10]2=[O:15])=[C:6]([CH3:8])[CH:7]=1Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 90 °C
Procedure
To a solution of 2-(4-bromo-2,6-dimethylphenyl)cyclopent-4-ene-1,3-dione (described in WO 2010/089210) (50 g, 0.18 mol) in acetic acid (2000 ml) at 25-30°C. is added zinc powder (82.3 g, 1.26 mol). The resulting suspension is heated to 90°C. for 2 hours, followed by cooling to room temperature then filtration through a bed of diatomaceous earth. The residue is washed with methanol (100 ml×2) and the solution is concentrated in vacuo. Distilled water is added and the crude product is extracted with ethyl acetate (500 ml×3). Organic fractions are combined then washed with distilled water, brine, then dried over sodium sulfate, filtered and the filtrate concentrated in vacuo to afford 2-(4-bromo-2,6-dimethylphenyl)cyclopentane-1,3-dione. This material is used directly in the next step without further purification.
Workup
- temperatureby cooling to room temperature
- filtrationfiltration through a bed of diatomaceous earth
- washThe residue is washed with methanol (100 ml×2)
- concentrationthe solution is concentrated in vacuo
- additionDistilled water is added
- extractionthe crude product is extracted with ethyl acetate (500 ml×3)
- washOrganic fractions are combined then washed with distilled water, brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationthe filtrate concentrated in vacuo
Sources & evidence
- ORD record
- ord-7ebb1a60483344098b2cc41164b2226e
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09107415B2
Reaction notes
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