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

HRID 1200161Notes

Reaction equation

HRID 1200161 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9].[F:12][C:13]([F:17])=[C:14]([F:16])[F:15].C1(O)C=CC=CC=1.[OH-].[K+]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[C:4]([O:11][C:14]([F:16])([F:15])[CH:13]([F:17])[F:12])[CH:5]=[CH:6][C:7]=1[N+:8]([O-:10])=[O:9]

Participants

7

Reactant 4

HCID 996PhenolHCID 8301TetrafluoroethyleneHCID 14797Potassium HydroxideHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 147216932-Fluoro-4-(1,1,2,2-tetrafluoroethoxy)nitrobenzeneYield 10.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

After dissolving 1.15 g of 3-fluoro-4-nitrophenol in 10 ml of dioxane, the resulting solution was violently stirred at about 60° C. for 15 minutes under the stream of a tetrafluoroethylene gas in large excess of said phenol. After quickly adding 0.04 g of potassium hydroxide, the solution was violently stirred for 2 hours under the same condition. The reaction solution was cooled, and after adding water, extracted with two 100-ml portions of diethyl ether. The ether layers were combined, dried and concentrated to obtain a yellow oily product as a residue. This oily product was subjected to chromatography on silica gel to obtain 0.20 g of 2-fluoro-4-(1,1,2,2-tetrafluoroethoxy)nitrobenzene.

Workup

  1. temperatureThe reaction solution was cooled
  2. extractionextracted with two 100-ml portions of diethyl ether
  3. customdried
  4. concentrationconcentrated
  5. customto obtain a yellow oily product as a residue

Sources & evidence

ORD record
ord-5420a0835764407c89f513e0c7bdd02d
Source dataset
uspto-grants-1990_02
Patent number
US04904696

Reaction notes

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