HCID 68486955, compound → 4-[4-(Trifluoromethoxy)phenoxy]pyridine

HRID 1799512Notes

Reaction equation

HRID 1799512 reaction equation
[F:1][C:2]([F:19])([F:18])[O:3][C:4]1[CH:17]=[CH:16][C:7]([O:8][C:9]2[CH:14]=[CH:13][N+:12]([O-])=[CH:11][CH:10]=2)=[CH:6][CH:5]=1.[H][H]>C(O)C.[Pd]>[F:19][C:2]([F:1])([F:18])[O:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]2[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 2

HCID 68486955HCID 68486955, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 453809774-[4-(Trifluoromethoxy)phenoxy]pyridineYield 100.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

After 4-[4-(Trifluoromethoxy)phenoxy]pyridine-N-oxide (130.0 g) was dissolved in ethanol (500 mL) and (50% wet) 5 w/w % palladium on carbon (6.5 g) was added. The resulting mixture was stirred under 3 atms of atmosphere of hydrogen at 27-49° C. for 6.5 hr. The reaction mixture was filtered to remove the catalyst followed by concentration in vacuo to give a quantitative yield (122.9 g) of pale yellow oily crude product. Purification by flash column chromatography (600 g of Silica Gel 60, spherical, ethyl acetate) afforded the pure target compound product as a colorless oil (86.74 g, 70.91% yield).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationfollowed by concentration in vacuo

Sources & evidence

ORD record
ord-ac8f4b5136af49acad017f3f383e4fad
Source dataset
uspto-grants-2013_01
Patent number
US08344148B2

Reaction notes

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