Methyl morpholine oxide → 2-Bromo-5-(trifluoromethyl)benzaldehyde

HRID 2197281Notes

Reaction equation

HRID 2197281 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[CH2:12][OH:13].C[N+]1([O-])CCOCC1>C(Cl)Cl.CC#N.[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:9])([F:10])[F:11])=[CH:4][C:3]=1[CH:12]=[O:13]

Participants

6

Reactant 2

HCID 82029Methyl morpholine oxideHCID 27562482-Bromo-5-(trifluoromethyl)benzyl alcohol

Product 1

HCID 70180472-Bromo-5-(trifluoromethyl)benzaldehyde

Reagents, catalysts & solvents 3

HCID 178419074HCID 178419074, compoundCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

To (2-bromo-5-trifluoromethyl-phenyl)-methanol (2.216 g, 8.69 mmol) and N-methylmorpholine N-oxide (2.051 g, 17.38 mmol) in CH2Cl2 (44 mL) and MeCN (2.2 mL) was added tetrapropylammonium perruthenate (0.311 g, 0.87 mmol), and the reaction was stirred at room temperature for 20 minutes. Once no starting material was seen by analytical tic, the mixture was concentrated and purified by silica gel chromatography to give the title compound.

Workup

  1. concentrationthe mixture was concentrated
  2. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-d7720d9e263a4d069f27e70daf3d4205
Source dataset
uspto-grants-2012_12
Patent number
US08338484B2

Reaction notes

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