Hydrochloric Acid → 1-Bromo-3,5-dichloro-2-methoxybenzene
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[OH:10].[C:11](=O)([O-])[O-].[K+].[K+].CI.Cl>CC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[O:10][CH3:11]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
2-Bromo-4,6-dichlorophenol (Preparation 24, 4.6 g, 19 mmol), potassium carbonate (4.5 g, 32.3 mmol) and methyl iodide (1.8 ml, 20.5 mmol) were combined in 46 ml acetone and heated to reflux for 18 hours. The reaction was cooled to 0° C., 1N HCl (aqueous) was added to give pH 3, and the reaction was extracted into 50 ml ethyl acetate. The organic layer was washed with brine (2×20 ml), dried over sodium sulphate and concentrated in vacuo to afford the title compound as a brown solid (5.5 g).
Workup
- temperatureheated
- temperatureto reflux for 18 hours
- customto give pH 3
- extractionthe reaction was extracted into 50 ml ethyl acetate
- washThe organic layer was washed with brine (2×20 ml)
- dry with materialdried over sodium sulphate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-e270c987cee64043a33661ecb3fdd6d6
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07572797B2
Reaction notes
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