Acetonitrile → 1-(2-Bromo-5-trifluoromethylphenyl)-ethanone

HRID 563505Notes

Reaction equation

HRID 563505 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[CH:12]([OH:14])[CH3:13].C[N+]1([O-])CCOCC1.CC#N>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:10])([F:11])[F:9])=[CH:4][C:3]=1[C:12](=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 82029Methyl morpholine oxideHCID 57458795HCID 57458795, compound

Product 1

HCID 574587961-(2-Bromo-5-trifluoromethylphenyl)-ethanone

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

1-(2-Bromo-5-trifluoromethyl-phenyl)-ethanol (0.914 g, 3.40 mmol), N-methylmorpholine N-oxide (0.731 g, 6.24 mmol), and tetrapropylammonium perruthenate (0.109 g, 0.31 mmol) were combined in CH2Cl2 (18 mL) and MeCN (0.9 mL) and stirred at room temperature for 30 minutes. Once no starting material was seen by analytical LCMS, the mixture was filtered through Celite and purified by silica gel chromatography (0-100% EtOAc in hexanes) to give the title compound.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. custompurified by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-d9fb8eb71a984664b489ebe5c104494c
Source dataset
uspto-grants-2011_11
Patent number
US08067445B2

Reaction notes

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