Cesium carbonate → 1-(4-Chlorobutoxy)-4-iodobenzene

HRID 215775Notes

Reaction equation

HRID 215775 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:15][CH2:16][CH2:17][CH2:18][CH2:19]I>C(#N)C>[Cl:15][CH2:16][CH2:17][CH2:18][CH2:19][O:8][C:5]1[CH:6]=[CH:7][C:2]([I:1])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 108944-IodophenolHCID 825271-Chloro-4-iodobutane

Product 1

HCID 581868981-(4-Chlorobutoxy)-4-iodobenzeneYield 99.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-iodophenol (1.0 g) in acetonitrile (10 mL), cesium carbonate (3.0 g) and 1-chloro-4-iodobutane (1.2 g) were added and the mixture was heated to 100° C., at which it was stirred for 4 hours. The reaction mixture was cooled to room temperature and filtered to remove insoluble materials, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=7:3 to 1:1) to give the titled compound (1.4 g, 99%) as a brown oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationfiltered
  3. customto remove insoluble materials
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: n-hexane:ethyl acetate=7:3 to 1:1)

Sources & evidence

ORD record
ord-707a7309f93648ceb4b2085229a321ba
Source dataset
uspto-grants-2012_06
Patent number
US08193176B2

Reaction notes

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