Chlorotrifluoroethylene → 3-(2-Chloro-1,1,2-trifluoroethoxy)benzenamine

HRID 597098Notes

Reaction equation

HRID 597098 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[OH-].[K+].[F:13][C:14]([F:18])=[C:15]([F:17])[Cl:16]>CN(C)C=O>[F:13][C:14]([F:18])([O:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[NH2:1])[CH:15]([F:17])[Cl:16]

Participants

5

Reactant 3

HCID 6594ChlorotrifluoroethyleneHCID 111373-NitrophenolHCID 14797Potassium Hydroxide

Product 1

HCID 132284973-(2-Chloro-1,1,2-trifluoroethoxy)benzenamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

139 grams (1 mole) of 3-nitro-phenol and 28 grams (0.5 mole) of potassium hydroxide were dissolved in 400 milliliters of dimethyl formamide, and 140 grams (1.2 mole) of trifluoro-chloroethylene were introduced in a gas pipe at 40° C; the mixture was then maintained at 60° C for 2 hours. The main amount of dimethyl formamide was distilled off in vacuo. The residue was poured into ice water, separated, dried over Na2SO4 and distilled in vacuo.

Workup

  1. distillationThe main amount of dimethyl formamide was distilled off in vacuo
  2. additionThe residue was poured into ice water
  3. customseparated
  4. dry with materialdried over Na2SO4
  5. distillationdistilled in vacuo

Sources & evidence

ORD record
ord-c57a8c91d447426f992018da8346e1a3
Source dataset
uspto-grants-1977_03
Patent number
US04013452

Reaction notes

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