Iodoethane → 1-Chloro-4-ethoxy-2-nitrobenzene

HRID 1274365Notes

Reaction equation

HRID 1274365 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[CH2:12](I)[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:12]([O:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([N+:9]([O-:11])=[O:10])[CH:4]=1)[CH3:13]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 691274-Chloro-3-nitrophenol

Product 1

HCID 2407341-Chloro-4-ethoxy-2-nitrobenzeneYield 97.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-chloro-3-nitrophenol (5.00 g, 29 mmol) in acetone (50 ml) were added ethyl iodide (4.95 g, 32 mmol) and potassium carbonate (4.37 g, 32 mmol), followed by stirring at room temperature for 20 hours. After filtration of the insoluble matter, the filtrate was subjected to evaporation under reduced pressure to remove the solvent, and the residue was purified by silica gel column chromatography (eluent; chloroform) to give 4-ethoxy-1-chloro-2-nitrobenzene (5.71 g).

Workup

  1. filtrationAfter filtration of the insoluble matter
  2. customthe filtrate was subjected to evaporation under reduced pressure
  3. customto remove the solvent
  4. customthe residue was purified by silica gel column chromatography (eluent; chloroform)

Sources & evidence

ORD record
ord-46792c3674284c289776725f648199e7
Source dataset
uspto-grants-2000_12
Patent number
US06156801

Reaction notes

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