4-Nitrophenol → 1-(2-Chloroethoxy)-4-nitrobenzene

HRID 639371Notes

Reaction equation

HRID 639371 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][CH2:19][Cl:20].[I-].[K+]>CC(C)=O.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:20][CH2:19][CH2:18][O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 9804-NitrophenolHCID 4875Potassium IodideHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium Carbonate

Product 1

HCID 27645871-(2-Chloroethoxy)-4-nitrobenzene

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Procedure

To the solution of 27.83 g (0.2 Mol) of 4-nitro-phenol (Fluka 73560) in 420 mL of acetone is added 55.28 g (0.4 Mol) of potassium carbonate, 143.42 g (1 Mol) of 1-bromo-2-chloro-ethane, 0.55 g (0.0033 Mol) of potassium iodide and 0.28 g (0.00087 Mol) of tetrabutyl-ammonium bromide (Fluka 86860). The resulting suspension is refluxed for 67 h. After removing the solvent under reduced pressure, the residue is taken up into ethyl acetate and washed with water. The combined organic layers are dried (Na2SO4), filtered and concentrated under reduced pressure. After trituration of the residue with ligroin, the crystals are filtered off to obtain 1-(2-chloro-ethoxy)-4-nitro-benzene.

Workup

  1. temperatureThe resulting suspension is refluxed for 67 h
  2. customAfter removing the solvent under reduced pressure
  3. washwashed with water
  4. dry with materialThe combined organic layers are dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. filtrationAfter trituration of the residue with ligroin, the crystals are filtered off

Sources & evidence

ORD record
ord-0a300830a82447e498e66d06eb759a1a
Source dataset
uspto-grants-2010_04
Patent number
US07691855B2

Reaction notes

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