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

HRID 1095829Notes

Reaction equation

HRID 1095829 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+]>CN(C=O)C.C(OCC)C>[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 82.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

4-Iodophenol (10 g, 45.4 mmol), 1-bromo-3-chloropropane (7 g, 50.0 mmol) and potassium carbonate (7.54 g, 54.5 mmol) were mixed in DMF, and stirred at room temperature for 15 hours. The reaction liquid was diluted with diethyl ether, washed with water and saturated saline in that order, and the organic layer was dried with sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was purified through silica gel column chromatography (eluate: ethyl acetate/hexane=5/95) to obtain the entitled compound (11.1 g, 82.3%) as a pale yellow solid.

Workup

  1. customThe reaction liquid
  2. washwashed with water and saturated saline in that order
  3. dry with materialthe organic layer was dried with sodium sulfate
  4. customThe solvent was evaporated off under reduced pressure
  5. customthe residue was purified through silica gel column chromatography (eluate: ethyl acetate/hexane=5/95)

Sources & evidence

ORD record
ord-c2dc4aeacf534af09102b1872a86f1de
Source dataset
uspto-grants-2012_03
Patent number
US08138206B2

Reaction notes

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