Potassium Iodide → 1-(2-chloroethoxy)-3-nitrobenzene

HRID 362308Notes

Reaction equation

HRID 362308 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=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:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 78491-Bromo-2-ChloroethaneHCID 111373-NitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 43044241-(2-chloroethoxy)-3-nitrobenzene

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 180AcetoneSolvent

Procedure

60 g of 3-nitrophenol, 88 g of potassium carbonate and 178 ml of 1-bromo-2-chloroethane are boiled under reflux for 36 h in 800 ml of acetone together with 1.5 g of tetrabutylammonium bromide and 2.0 g of potassium iodide. The mixture is then cooled to RT and concentrated in an RE. The mixture is treated with water, extracted 3 times with ethyl acetate and concentrated. The residue is chromatographed using methylene chloride and the product-containing fractions are concentrated. 1-(2-chloroethoxy)-3-nitrobenzene are obtained as an oil which may crystallize (m.p. 58°-60° C).

Workup

  1. concentrationconcentrated in an RE
  2. additionThe mixture is treated with water
  3. extractionextracted 3 times with ethyl acetate
  4. concentrationconcentrated
  5. customThe residue is chromatographed
  6. concentrationthe product-containing fractions are concentrated

Sources & evidence

ORD record
ord-99657582825341e6a9fa013d11a586f9
Source dataset
uspto-grants-1999_02
Patent number
US05869485

Reaction notes

Loading…