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

HRID 2409517Notes

Reaction equation

HRID 2409517 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 2-bromo-5-trifluoromethyl-benzaldehyde.

Workup

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

Sources & evidence

ORD record
ord-da120e4b0a554e90ab30064bd5613d24
Source dataset
uspto-grants-2014_08
Patent number
US08815917B2

Reaction notes

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