1-Bromo-3-chloropropane → 1-(3-Chloropropoxy)-4-iodobenzene

HRID 548623Notes

Reaction equation

HRID 548623 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Br[CH2:16][CH2:17][CH2:18][Cl:19]>CC(C)=O>[Cl:19][CH2:18][CH2:17][CH2:16][O:14][C:11]1[CH:12]=[CH:13][C:8]([I:7])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 108944-IodophenolHCID 11430Potassium Carbonate

Product 1

HCID 158955201-(3-Chloropropoxy)-4-iodobenzeneYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Potassium carbonate (6.3 g, 45.4 mmol, 2 eq) is added to a solution of 4-iodophenol a1 (5 g, 22.7 mmol, 1 eq) in acetone (200 ml) then 1-bromo-3-chloropropane a2 (2.2 ml, 22.7 mmol, 1 eq) is added and the mixture is heated at reflux overnight. The solvent is then removed in vacuo, and the residue is dissolved into dichloromethane. The organic layer is washed twice with a saturated solution of aqueous ammonium chloride then the aqueous layer is extracted with dichloromethane. The organic layers are dried over magnesium sulfate and concentrated in vacuo to give 6.6 g of 1-(3-chloropropoxy)-4-iodobenzene a3 as a colorless oil.

Workup

  1. temperaturethe mixture is heated
  2. temperatureat reflux overnight
  3. customThe solvent is then removed in vacuo
  4. dissolutionthe residue is dissolved into dichloromethane
  5. washThe organic layer is washed twice with a saturated solution of aqueous ammonium chloride
  6. extractionthe aqueous layer is extracted with dichloromethane
  7. dry with materialThe organic layers are dried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bd1369a3fa354d22b846c72912602be7
Source dataset
uspto-grants-2011_05
Patent number
US07943605B2

Reaction notes

Loading…