Hydrogen Peroxide → 4-(4-(Trifluoromethyl)phenyl)pyridine 1-oxide

HRID 2105618Notes

Reaction equation

HRID 2105618 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[OH:17]O>C[Re](=O)(=O)=O.C(Cl)Cl>[F:16][C:2]([F:1])([F:15])[C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[CH:11][N+:12]([O-:17])=[CH:13][CH:14]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 6139654-(4-Trifluoromethylphenyl)pyridine

Product 1

HCID 573508294-(4-(Trifluoromethyl)phenyl)pyridine 1-oxide

Reagents, catalysts & solvents 2

HCID 178477782HCID 178477782, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(4-trifluoromethyl-phenyl)-pyridine (5.0 g, 22 mmol) and methyltrioxorhenium (VII) (Aldrich) (110 mg, 0.45 mmol) in a 100-mL, round-bottomed flask was added CH2Cl2 (10 mL). Hydrogen peroxide (5 mL, Aldrich) was added drop-wise, and the reaction was stirred at room temperature under N2 for 48 h. The mixture was partitioned between CH2Cl2 and brine, and the aqueous layer was extracted with CH2Cl2 (40 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to give the title compound as an off-white solid. MS (ESI, pos. ion) m/z: 240 (M+1).

Workup

  1. customThe mixture was partitioned between CH2Cl2 and brine
  2. extractionthe aqueous layer was extracted with CH2Cl2 (40 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff70fb4373844606a1d89fcb185ae9db
Source dataset
uspto-grants-2009_08
Patent number
US07579347B2

Reaction notes

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