Hydrochloric Acid → Methyl (4-chloro-2-iodophenoxy)acetate
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]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
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
- temperaturewas heated
- temperatureunder reflux for 2 h
- extractionthe mixture was extracted with ether (three times)
- dry with materialThe organic extracts were dried (MgSO4)
- customevaporated
- 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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