4-Nitrophenol → 1-(2-Bromo-1,1,2-trifluoroethoxy)-4-nitrobenzene

HRID 1583282

Reaction equation

HRID 1583282 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-].[K+].[Br:13][C:14]([F:18])=[C:15]([F:17])[F:16]>CN(C)C=O>[Br:13][CH:14]([F:18])[C:15]([F:17])([F:16])[O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 117301-Bromo-1,2,2-trifluoroetheneHCID 14797Potassium Hydroxide

Product 1

HCID 132284951-(2-Bromo-1,1,2-trifluoroethoxy)-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

278 g of 4-nitrophenol and 56 g of potassium hydroxide were dissolved in 800 ml of dimethylformamide, 179 g of bromotrifluoroethylene were fed in, a little at a time, at 40° C., and stirring was then continued for 2 hours at 60° C. The solvent was removed under reduced pressure in a rotary evaporator, the residue was poured into ice-water and extracted with 3×500 ml of methylene chloride, the extract was washed with dilute sodium hydroxide solution and water and dried over Na2SO4, and the solvent was removed. When the residue was distilled, 279.5 g of pure product passed over at 114° C./1.3 mbar.

Workup

  1. customThe solvent was removed under reduced pressure in a rotary evaporator
  2. additionthe residue was poured into ice-water
  3. extractionextracted with 3×500 ml of methylene chloride
  4. washthe extract was washed with dilute sodium hydroxide solution and water
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed
  7. distillationWhen the residue was distilled
  8. custompassed over at 114° C./1.3 mbar

Sources & evidence

ORD record
ord-9743f657a1bb436fa06a197d84f451d0
Source dataset
uspto-grants-1985_11
Patent number
US04551448

Linked notes

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