Potassium Iodide → 1-(3-Bromopropoxy)-3-nitrobenzene

HRID 1607161Notes

Reaction equation

HRID 1607161 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[N+:14]([C:17]1[CH:18]=[C:19]([OH:23])[CH:20]=[CH:21][CH:22]=1)([O-:16])=[O:15]>CC(C)=O>[Br:1][CH2:2][CH2:3][CH2:4][O:23][C:19]1[CH:18]=[C:17]([N+:14]([O-:16])=[O:15])[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 80011,3-DibromopropaneHCID 111373-NitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 71723011-(3-Bromopropoxy)-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

43 ml of 1,3-dibromopropane are added to a suspension of 29 g of potassium carbonate and 0.5 g of potassium iodide in 170 ml of acetone and the whole is heated under reflux. A solution of 19.4 g of 3-nitrophenol is then added dropwise thereto in the course of 2 hours and the whole is heated for a further 15 hours under reflux. The reaction mixture is filtered while hot and concentrated by evaporation. After chromatography of the residue over silica gel using toluene, 3-(3-bromopropoxy)-nitrobenzene is obtained in the form of a light yellow oil.

Workup

  1. temperaturethe whole is heated
  2. temperatureunder reflux
  3. temperaturein the course of 2 hours and the whole is heated for a further 15 hours
  4. temperatureunder reflux
  5. filtrationThe reaction mixture is filtered while hot and
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-86790444b3984350a7417d8f286d44c9
Source dataset
uspto-grants-1989_09
Patent number
US04863942

Reaction notes

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