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

HRID 1919922Notes

Reaction equation

HRID 1919922 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 tlc, 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-433d39fd74e14681a0de8234dfcf360a
Source dataset
uspto-grants-2012_05
Patent number
US08168678B2

Reaction notes

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