Water → 2-(4-Iodophenoxy)ethanol

HRID 1916691Notes

Reaction equation

HRID 1916691 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][OH:12].C([O-])([O-])=O.[K+].[K+].O>CC(C)=O>[I:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 108944-IodophenolHCID 108982-BromoethanolHCID 11430Potassium Carbonate

Product 1

HCID 35132082-(4-Iodophenoxy)ethanol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 11 g (50 mmol) 4-iodophenol, 3.88 mL (55 mmol) 2-bromoethanol and 8.3 g (60 mmol) K2CO3 in 60 mL acetone is refluxed for 24 h. The solvent is eliminated i.vac., the residue is combined with water, exhaustively extracted with EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography on silica gel (cyc/EtOAc 7:3).

Workup

  1. temperatureis refluxed for 24 h
  2. extractionexhaustively extracted with EtOAc
  3. dry with materialthe organic phase is dried over Na2SO4
  4. customis purified by chromatography on silica gel (cyc/EtOAc 7:3)

Sources & evidence

ORD record
ord-447f97c3983745dd9feacbbcdd557cf1
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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