Hydrochloric Acid → 2-Fluoro-4-(1,1,2,2-tetrafluoroethoxy)aniline

HRID 466798Notes

Reaction equation

HRID 466798 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:17])([F:16])[CH:13]([F:15])[F:14])=[CH:7][C:6]=1[F:18])(=O)C.Cl.C(=O)([O-])O.[Na+]>>[F:18][C:6]1[CH:7]=[C:8]([O:11][C:12]([F:16])([F:17])[CH:13]([F:15])[F:14])[CH:9]=[CH:10][C:5]=1[NH2:4]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 147216944-Acetylamino-3-fluoro-1-(1,1,2,2-tetrafluoroethoxy)benzene

Product 1

HCID 146245342-Fluoro-4-(1,1,2,2-tetrafluoroethoxy)anilineYield 81%

Procedure

0.60 Gram of 4-acetylamino-3-fluoro-1-(1,1,2,2-tetrafluoroethoxy)benzene and 10 ml of a 20% aqueous hydrochloric acid were added to a reactor and stirred under reflux for 2 hours. After cooling the reaction solution, a 5% aqueous sodium hydrogencarbonate solution was added to make the solution weakly alkaline. The reaction solution was then 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 0.40 g of 2-fluoro-4-(1,1,2,2-tetrafluoroethoxy)aniline.

Workup

  1. temperatureunder reflux for 2 hours
  2. temperatureAfter cooling the reaction solution
  3. extractionThe reaction solution was then extracted with two 100-ml portions of diethyl ether
  4. customdried
  5. concentrationconcentrated
  6. customto obtain a yellow oily product as a residue

Sources & evidence

ORD record
ord-585d398ab87348a1abef7e589bc3f6bf
Source dataset
uspto-grants-1992_10
Patent number
US05157155

Reaction notes

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