Trifluoroacetic anhydride → 2-[3-(2-Nitrophenoxy)phenoxy]propionitrile

HRID 1609263Notes

Reaction equation

HRID 1609263 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=1)[O:10][CH:11]([CH3:15])[C:12]([NH2:14])=O)([O-:3])=[O:2].FC(F)(F)C(OC(=O)C(F)(F)F)=O>N1C=CC=CC=1.O1CCOCC1>[N+:1]([C:4]1[CH:22]=[CH:21][CH:20]=[CH:19][C:5]=1[O:6][C:7]1[CH:8]=[C:9]([CH:16]=[CH:17][CH:18]=1)[O:10][CH:11]([CH3:15])[C:12]#[N:14])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 200843872-[3-(2-Nitrophenoxy)phenoxy]propionamide

Product 1

HCID 200844962-[3-(2-Nitrophenoxy)phenoxy]propionitrileYield 100.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

In a mixture of 12 ml of pyridine and 35 ml of dioxane was suspended 4.55 g of 2-[3-(2-nitrophenoxy)phenoxy]propionamide and, then, 3.6 g of trifluoroacetic anhydride was added dropwise with ice-cooling and stirring. The mixture was then stirred at that temperature for 30 minutes and, following addition of ice-water, extracted with ether. The ether extract was washed with diluted hydrochloric acid and sodium hydrogen carbonate solution in that order, dried and concentrated to give 4.3 g of the title compound as a light yellow oil.

Workup

  1. temperaturecooling
  2. stirringThe mixture was then stirred at that temperature for 30 minutes
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwas washed with diluted hydrochloric acid and sodium hydrogen carbonate solution in that order
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-813a322781a5422fa36680d115afb337
Source dataset
uspto-grants-1995_03
Patent number
US05399703

Reaction notes

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