Aniline, 2,3,4,5-tetrafluoro- (8CI) → HCID 18948775, compound

HRID 1768552Notes

Reaction equation

HRID 1768552 reaction equation
[F:1][C:2]1[C:8]([F:9])=[C:7]([F:10])[C:6]([F:11])=[CH:5][C:3]=1[NH2:4].Cl[S:13]([OH:16])(=[O:15])=[O:14]>ClC(Cl)=C(Cl)Cl>[NH2:4][C:3]1[C:2]([F:1])=[C:8]([F:9])[C:7]([F:10])=[C:6]([F:11])[C:5]=1[S:13]([OH:16])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 21757Aniline, 2,3,4,5-tetrafluoro- (8CI)HCID 24638Chlorosulfonic acid

Product 1

HCID 18948775HCID 18948775, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 31373TetrachloroethyleneSolvent

Procedure

2,3,4,5-Tetrafluoroaniline (16.5 g, 0.1 mol) was added dropwise over 20 minutes with stirring to a mixture of chlorosulfonic acid (14 g, 0.12 mol) in tetrachloroethylene (100 mL) with ice bath cooling. A yellow precipitate formed immediately.. When the addition was complete, the mixture was heated at reflux for three hours, during which a light tan granular solid formed. The solid was collected by filtration, washed with ether, and dried in vacuo to give the title compound (25 g); m.p. 272°-276° .

Workup

  1. temperaturecooling
  2. customA yellow precipitate formed immediately
  3. additionWhen the addition
  4. temperaturethe mixture was heated
  5. temperatureat reflux for three hours, during which a light tan granular solid
  6. customformed
  7. filtrationThe solid was collected by filtration
  8. washwashed with ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-bf96309d6d084c3ebfda1d75022c01d7
Source dataset
uspto-grants-1995_01
Patent number
US05378704

Reaction notes

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