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

HRID 1695127Notes

Reaction equation

HRID 1695127 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-30d0839d0b5342eea5331aedeb3431ea
Source dataset
uspto-grants-2012_04
Patent number
US08163727B2

Reaction notes

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