Hydrochloric Acid → 4-Chloro-3-iodophenol
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8]C)=[CH:4][C:3]=1[I:10].C(=O)([O-])O.[Na+].Cl>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[I:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-chloro-2-iodo-4-methoxybenzene (2.68 g, 10.0 mmol) in dichloromethane (20 ml) was dropped under ice cooling 0.91M boron tribromide in dichloromethane (13.0 ml, 12.0 mmol). The mixture was stirred for 1 hour under ice cooling and for a day at room temperature. To the reaction mixture was added an aqueous saturated sodium hydrogencarbonate solution. The mixture was acidified with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with an aqueous saturated sodium chloride solution and dried over sodium sulfate. The solvent was removed to give the subject compound as pale brown crystals (2.61 g, quantitatively).
Workup
- extractionextracted with ethyl acetate
- washThe organic layer was washed with an aqueous saturated sodium chloride solution
- dry with materialdried over sodium sulfate
- customThe solvent was removed
Sources & evidence
- ORD record
- ord-04e55c6b9c5b41b5ac88bc802f496fc1
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07220773B2
Reaction notes
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