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

HRID 1023773Notes

Reaction equation

HRID 1023773 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-2a5de9f6bf3444e5a3bee329e61c8d6c
Source dataset
uspto-grants-2014_05
Patent number
US08722741B2

Reaction notes

Loading…