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

HRID 33692Notes

Reaction equation

HRID 33692 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Br[CH2:10][CH2:11][CH2:12][Cl:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:13][CH2:12][CH2:11][CH2:10][O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

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

Product 1

HCID 158955201-(3-Chloropropoxy)-4-iodobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 4-iodophenol (20 g), 1-bromo-3-chloropropane (18 mL), and potassium carbonate (38 g) in acetone (250 mL) was heated at reflux for 16 h and allowed to cool to room temperature. The suspension was filtered, and the filtrate was evaporated in vacuo. Kugelrohr distillation of the residue (5-10 mm Hg, 210° C.) gave the title compound as a white crystalline solid (22 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 h
  3. filtrationThe suspension was filtered
  4. customthe filtrate was evaporated in vacuo
  5. distillationKugelrohr distillation of the residue (5-10 mm Hg, 210° C.)

Sources & evidence

ORD record
ord-888dd3295b454d21b5a18102c269fa38
Source dataset
uspto-grants-2008_09
Patent number
US07429586B2

Reaction notes

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