4-Aminophenol → 4-(1,1,2-Trifluoroethoxy)aniline

HRID 1655550Notes

Reaction equation

HRID 1655550 reaction equation
[F:1][CH:2]=[C:3]([F:5])[F:4].[CH:6]1[C:11]([NH2:12])=[CH:10][CH:9]=[C:8]([OH:13])[CH:7]=1.[OH-].[K+]>CN(C=O)C>[F:4][C:3]([F:5])([O:13][C:8]1[CH:9]=[CH:10][C:11]([NH2:12])=[CH:6][CH:7]=1)[CH2:2][F:1]

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 9665TrifluoroethyleneHCID 14797Potassium Hydroxide

Product 1

HCID 197926734-(1,1,2-Trifluoroethoxy)anilineYield 25%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Gaseous trifluoroethylene was bubbled into a mixture of 7.0 g (64.1 mmol) of p-aminophenol, 0.7 g (12.8 mmol) of powdered KOH, and 70 ml dry DMF at 90° C. for 11/4 hours. The mixture was poured into ice water and extracted 2 times with ether. The combined ether layers were washed with diluted aqueous NaOH, washed with water, dried over MgSO4 and filtered. HCl was bubbled into the ether solution. The resulting gray solid was collected by filtration to give 3.6 g (25 percent of theoretical) of the above-named aniline as the HCl salt along with a 20 percent impurity of 4-(1,2-difluoroethenyloxy)benzene-amine.

Workup

  1. extractionextracted 2 times with ether
  2. washThe combined ether layers were washed with diluted aqueous NaOH
  3. washwashed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customHCl was bubbled into the ether solution
  7. filtrationThe resulting gray solid was collected by filtration

Sources & evidence

ORD record
ord-b6d402b15d8b4fe29491860fc02ae96b
Source dataset
uspto-grants-1993_10
Patent number
US05250690

Reaction notes

Loading…