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

HRID 1810266Notes

Reaction equation

HRID 1810266 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 (0331 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-d645f9ba546e40b7870fb2ebd1abf851
Source dataset
uspto-grants-2013_01
Patent number
US08362044B2

Reaction notes

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