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

HRID 1693077Notes

Reaction equation

HRID 1693077 reaction equation
Br[CH2:2][CH2:3][CH2:4][Cl:5].C(=O)([O-])[O-].[K+].[K+].[I:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1>CC(C)=O>[Cl:5][CH2:4][CH2:3][CH2:2][O:19][C:16]1[CH:17]=[CH:18][C:13]([I:12])=[CH:14][CH:15]=1

Participants

5

Reactant 3

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

Product 1

HCID 158955201-(3-Chloropropoxy)-4-iodobenzeneYield 111.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1-Bromo-3-chloropropane (21.4 g, 136 mmol) and potassium carbonate (30 g, 217 mmol) were added to an acetone (300 mL) solution of 4-iodophenol (20 g, 90.9 mmol), and stirred under reflux for 20 hours. The reaction mixture was cooled to room temperature, filtered, and the filtrate was concentrated under reduced pressure to obtain the entitled compound (30 g, 100%).

Workup

  1. temperatureunder reflux for 20 hours
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bd7e7f75ef6649fb83ee06b3066900bf
Source dataset
uspto-grants-2012_04
Patent number
US08158652B2

Reaction notes

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