4-Aminophenol → 4-(1,1-Difluoro-2,2,2-trichloroethoxy)aniline

HRID 1655548

Reaction equation

HRID 1655548 reaction equation
[CH:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[C:3]([OH:8])[CH:2]=1.[H-].[Na+].[F:11][C:12](Cl)([F:17])[C:13]([Cl:16])([Cl:15])[Cl:14]>CS(C)=O>[F:11][C:12]([F:17])([O:8][C:3]1[CH:4]=[CH:5][C:6]([NH2:7])=[CH:1][CH:2]=1)[C:13]([Cl:16])([Cl:15])[Cl:14]

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 64261,1,1,2-Tetrachloro-2,2-difluoroethaneHCID 24758Sodium hydride

Product 1

HCID 135292554-(1,1-Difluoro-2,2,2-trichloroethoxy)aniline

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2.0 g (18.3 mmol) of p-aminophenol was added over a period of 10 minutes to a mixture of 0.48 g (20.1 mmol) of sodium hydride in 20 ml of dry DMSO. The mixture was stirred for 20 minutes. 3.73 g (18.3 mmol) of 1,1-difluoro-tetrachloroethane was added causing an exotherm to 47° C. The mixture was stirred at 60° C. for 2 hours, then poured into ice water. The brown solid was collected by filtration, dried, dissolved in ether and then HCl gas was bubbled into the solution causing the above-named aniline to precipitate as the hydrochloride salt. The white solid (4.4 g, 87 percent of theoretical d 250° C.) was collected by filtration.

Workup

  1. customto 47° C
  2. stirringThe mixture was stirred at 60° C. for 2 hours
  3. filtrationThe brown solid was collected by filtration
  4. customdried
  5. dissolutiondissolved in ether
  6. customHCl gas was bubbled into the solution
  7. customto precipitate as the hydrochloride salt
  8. filtrationThe white solid (4.4 g, 87 percent of theoretical d 250° C.) was collected by filtration

Sources & evidence

ORD record
ord-ce4291de36e44412b9bd74ae5712ae97
Source dataset
uspto-grants-1993_10
Patent number
US05250690

Linked notes

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