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

HRID 1364208Notes

Reaction equation

HRID 1364208 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(=O)CC.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

6

Reactant 3

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

Product 1

HCID 158955201-(3-Chloropropoxy)-4-iodobenzeneYield 105.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-iodophenol (20.0 g) and 1-bromo-3-chloropropane (18.6 g) in 2-butanone (200 mL), potassium carbonate (25.1 g) was added and stirred at 100° C. for 5 hours. The reaction mixture was cooled to room temperature, diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure to give the titled compound (28.4 g) as an orange-colored oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c5668ab52400415c934900457a99a410
Source dataset
uspto-grants-2011_02
Patent number
US07888354B2

Reaction notes

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