Phenol → 2-Fluoro-4-(1,1,2,2-tetrafluoroethoxy)aniline

HRID 1200167Notes

Reaction equation

HRID 1200167 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[NH2:8].[OH-].[K+].[F:12][C:13]([F:17])=[C:14]([F:16])[F:15].C1(O)C=CC=CC=1>O.CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([O:9][C:14]([F:16])([F:15])[CH:13]([F:17])[F:12])[CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

7

Reactant 4

HCID 996PhenolHCID 8301TetrafluoroethyleneHCID 14797Potassium HydroxideHCID 27359194-Amino-3-fluorophenol

Product 1

HCID 146245342-Fluoro-4-(1,1,2,2-tetrafluoroethoxy)anilineYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.70 Gram of 3-fluoro-4-aminophenol, 0.06 g of potassium hydroxide and 10 ml of dimethylformamide were added to a reactor and stirred for 20 minutes at an oil bath temperature of from 60° to 70° C. This solution was then violently stirred at the same temperature for 2 hours under the stream of a tetrafluoroethylene gas in excess of said phenol. The reaction solution was cooled and after adding water, extracted with two 150-ml portions of diethyl ether. The ether layers were combined, washed with water, dried and concentrated to obtain a crude porduct. This crude product was subjected to chromatography on silica gel to obtain 1.00 g of 2-fluoro-4-(1,1,2,2-tetrafluoroethoxy)aniline.

Workup

  1. temperatureThe reaction solution was cooled
  2. extractionextracted with two 150-ml portions of diethyl ether
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customto obtain a crude porduct

Sources & evidence

ORD record
ord-05e1866528c9473d8fff816dccb7bfed
Source dataset
uspto-grants-1990_02
Patent number
US04904696

Reaction notes

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