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

HRID 38702

Reaction equation

HRID 38702 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[CH2:4][OH:5].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:9]=[CH:8][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:6][C:3]=1[CH:4]=[O:5]

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

2-Bromo-5-(trifluoromethyl)benzyl alcohol (2.216 g, 8.69 mmol) and N-methylmorpholine-N-oxide (2.051 g, 17.38 mmol) were combined in CH2Cl2 (44 mL) and MeCN (2.2 mL). Tetrapropylammonium perruthenate (0.311 g, 0.87 mmol) was added, and the reaction was stirred for 20 minutes at room temperature. Once no starting material was seen by analytical tlc, the mixture was concentrated, and the residue was purified by silica gel chromatography to give the title compound.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3b24e4b4e1b945c3aacdfacc4a0d6bd9
Source dataset
uspto-grants-2013_09
Patent number
US08524748B2

Linked notes

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