Tetrafluoroethylene → 3-Chloro-4-(1',1',2',2'-tetrafluoroethoxy)nitrobenzene

HRID 2254116Notes

Reaction equation

HRID 2254116 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].[OH-].[K+].[F:14][C:15]([F:19])=[C:16]([F:18])[F:17]>CN(C)C=O.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][C:16]([F:18])([F:17])[CH:15]([F:19])[F:14]

Participants

6

Reactant 3

HCID 8301TetrafluoroethyleneHCID 12074NitrofunginHCID 14797Potassium Hydroxide2×

Product 1

HCID 197442343-Chloro-4-(1',1',2',2'-tetrafluoroethoxy)nitrobenzene

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

20 Grams of 2-chloro-4-nitrophenol was dissolved in 200 ml of N,N-dimethylformamide, and 3.4 g of potassium hydroxide was added thereto. Tetrafluoroethylene was blown into the resulting solution at an inner temperature of 50° C., after which stirring was continued for 50 minutes at an inner temperature of 50° C. Thereafter, 3.5 g of potassium hydroxide was added to the stirred solution and the resulting solution was further stirred for 6 hours at an inner temperature of 100° C. The reaction solution was poured into ice water and extracted with ether. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated. The residue obtained wa subjected to column chromatography on silica gel with chloroform as an eluent to obtain 12.55 g of 3-chloro-4-(1',1',2',2'-tetrafluoroethoxy)nitrobenzene. 1H-NMR (CDCl3): δ(ppm) 8.37(1H, d, J=3 Hz), 8.20(1H, dd, J=9, 3 Hz), 7.57(1H, d, J=9 Hz), 6.07(1H, tt, J=53, 3 Hz)

Workup

  1. customwas blown into the resulting solution at an inner temperature of 50° C.
  2. stirringthe resulting solution was further stirred for 6 hours at an inner temperature of 100° C
  3. extractionextracted with ether
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue obtained

Sources & evidence

ORD record
ord-e333fba5f94e4cf2be9229f6c6d163ca
Source dataset
uspto-grants-1993_08
Patent number
US05234938

Reaction notes

Loading…