Dimethyl Sulfoxide → 2-[2-(5-Bromo-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

HRID 2106014Notes

Reaction equation

HRID 2106014 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3](=[O:17])[CH2:4][C:5]([C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:9]=1[O:15][CH3:16])([CH3:7])[CH3:6].[CH3:20]S(C)=O>>[Br:14][C:12]1[CH:11]=[CH:10][C:9]([O:15][CH3:16])=[C:8]([C:5]([CH3:7])([CH3:6])[CH2:4][C:3]2([C:2]([F:1])([F:18])[F:19])[CH2:20][O:17]2)[CH:13]=1

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 46938920HCID 46938920, compound

Product 1

HCID 578097532-[2-(5-Bromo-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane

Procedure

To a solution of 1,1,1-trifluoro-4-(5-bromo-2-methoxyphenyl)-4-methylpentan-2-one (5 g, 14.7 mmol) in 5 mL of anhydrous DMSO at room temperature was added 14.6 mL of the ylide stock solution (17.3 mmol) over 5 minutes. The reaction was quenched after 2 hours with water and diethyl ether. The aqueous layer was extracted with diethyl ether. The combined organic layers were washed with water and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 2-[2-(5-bromo-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane as a dark yellow oil.

Workup

  1. customThe reaction was quenched after 2 hours with water and diethyl ether
  2. extractionThe aqueous layer was extracted with diethyl ether
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f94526d6f414b84b75d2f16ab78fcb4
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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