5-Fluoro-2-(2,2,2-trifluoroethoxy)nitrobenzene → 5-Fluoro-2-(2,2,2-trifluoroethoxy)aniline

HRID 2185920Notes

Reaction equation

HRID 2185920 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]([F:16])([F:15])[F:14])=[C:6]([N+:8]([O-])=O)[CH:7]=1>C(OCC)(=O)C.[Ni]>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH2:12][C:13]([F:14])([F:15])[F:16])=[C:6]([CH:7]=1)[NH2:8]

Participants

4

Reactant 1

HCID 234479215-Fluoro-2-(2,2,2-trifluoroethoxy)nitrobenzene

Product 1

HCID 174854135-Fluoro-2-(2,2,2-trifluoroethoxy)anilineYield 90.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
22.5 °C

Procedure

A mixture of 0.66 g of Compound 8A and 0.07 g of Raney-Nickel in 20 mL of ethyl acetate was stirred for 14 hours at 20-25° C. The catalyst was filtered off. The mixture was diluted with water. The organic layer was separated and the mixture extracted with 2×40 mL of ethyl acetate. The combined organic layers were washed with 20 mL of brine, dried over sodium sulphate and evaporated to dryness in vacuo to afford 0.52 g (90.6%) of Compound 8B as an oil.

Workup

  1. filtrationThe catalyst was filtered off
  2. additionThe mixture was diluted with water
  3. customThe organic layer was separated
  4. extractionthe mixture extracted with 2×40 mL of ethyl acetate
  5. washThe combined organic layers were washed with 20 mL of brine
  6. dry with materialdried over sodium sulphate
  7. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-e59feff57bef42659ba9126a19a4b812
Source dataset
uspto-grants-2002_06
Patent number
US06403594B1

Reaction notes

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