3-Iodophenol → Methyl alpha-(3-iodophenoxy)crotonate

HRID 1603163Notes

Reaction equation

HRID 1603163 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[OH-].[K+].Br/[C:12](/[CH3:18])=[CH:13]\[C:14]([O:16][CH3:17])=[O:15]>CN(C)C=O>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8]/[C:13](=[CH:12]\[CH3:18])/[C:14]([O:16][CH3:17])=[O:15]

Participants

5

Reactant 3

HCID 122723-IodophenolHCID 14797Potassium HydroxideHCID 12625788Methyl 3-bromocrotonate

Product 1

HCID 67599411Methyl alpha-(3-iodophenoxy)crotonate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 11 g (0.05 mol) of 3-iodophenol is added dropwise at 0 to 5° C. to a solution of 3 g (0.055 mol) of KOH in 30 ml of dimethylformamide. 9 g (0.05 mol) of methyl 3-bromocrotonate are added at this temperature, and stirring of the solution is continued for one hour at room temperature. The mixture is treated with ice-water and extracted using methyl tert-butyl ether, and the methyl tert-butyl ether phase is dried over Na2SO4 and concentrated in vacuo. The residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate: 99/1). This gives 9.7 g (61% of theory) of the title compound as an oil.

Workup

  1. extractionextracted
  2. dry with materialthe methyl tert-butyl ether phase is dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by chromatography on silica gel (cyclohexane/ethyl acetate: 99/1)

Sources & evidence

ORD record
ord-7c9de29803b94b7d80daf6d5dd412abf
Source dataset
uspto-grants-1999_11
Patent number
US05985919

Reaction notes

Loading…