Toluene → 1,3-Dichloro-5-isocyanato-2-(1,1,2,2-tetrafluoroethoxy)benzene

HRID 2290714Notes

Reaction equation

HRID 2290714 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:16])[C:8]=1[O:9][C:10]([F:15])([F:14])[CH:11]([F:13])[F:12])[NH2:5].C1(C)C=CC=CC=1.[C:24](Cl)(Cl)=[O:25].O1CCOCC1>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([N:5]=[C:24]=[O:25])[CH:6]=[C:7]([Cl:16])[C:8]=1[O:9][C:10]([F:14])([F:15])[CH:11]([F:13])[F:12]

Participants

6

Reactant 4

HCID 1140TolueneHCID 6371PhosgeneHCID 312751,4-DioxaneHCID 54637633,5-Dichloro-4-(1,1,2,2-tetrafluoroethoxy)aniline

Product 1

HCID 202301521,3-Dichloro-5-isocyanato-2-(1,1,2,2-tetrafluoroethoxy)benzene

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent2×

Procedure

33.4 g of 3,5-dichloro-4-(1,1,2,2,-tetrafluoroethoxy)aniline are dissolved in 130 ml of chlorobenzene. With stirring, this solution is added dropwise at 22° C. to a solution consisting of 90 g of toluene containing 20% by weight of phosgene and of 100 ml of dioxane and 300 ml of chlorobenzene. The reaction mixture is stirred for 1 hour at room temperature, 1 hour at 50° C. and then 1 hour at 80° C. The reaction mixture is subsequently concentrated in a water-jet vacuum and then distilled under high vacuum, affording the title compound of the formula ##STR8## as a colourless oil. Boiling point 81°-83° C./2.5 mbar.

Workup

  1. additionthis solution is added dropwise at 22° C. to a solution
  2. stirringThe reaction mixture is stirred for 1 hour at room temperature, 1 hour at 50° C.
  3. custom1 hour
  4. customat 80° C
  5. concentrationThe reaction mixture is subsequently concentrated in a water-jet vacuum
  6. distillationdistilled under high vacuum

Sources & evidence

ORD record
ord-fb294e807b9940a6a7d32f33580ea77c
Source dataset
uspto-grants-1986_10
Patent number
US04618608

Reaction notes

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