Hydrochloric Acid → Methyl (4-chloro-2-iodophenoxy)acetate

HRID 16081Notes

Reaction equation

HRID 16081 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([I:9])=[C:6]([OH:8])[CH:7]=1.Br[CH2:11][C:12]([O:14][CH3:15])=[O:13].C(=O)([O-])[O-].[K+].[K+].[ClH:22]>C(#N)C>[Cl:22][C:3]1[CH:2]=[CH:7][C:6]([O:8][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[C:5]([I:9])[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 66133335-chloro-2-iodophenol

Product 1

HCID 12079772Methyl (4-chloro-2-iodophenoxy)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-chloro-2-iodophenol (4.95 g), methyl bromoacetate (1.85 ml) and potassium carbonate (2.79 g) in acetonitrile (20 ml) was heated under reflux for 2 h. Aq HCl was added and the mixture was extracted with ether (three times). The organic extracts were dried (MgSO4), evaporated and purified by chromatography (silica, petrol ether as eluent) to give the sub-title compound (5.75 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. extractionthe mixture was extracted with ether (three times)
  4. dry with materialThe organic extracts were dried (MgSO4)
  5. customevaporated
  6. custompurified by chromatography (silica, petrol ether as eluent)

Sources & evidence

ORD record
ord-ff8cd44555e645b4b5e07ae7d5a0b751
Source dataset
uspto-grants-2010_06
Patent number
US07737135B2

Reaction notes

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