Methyl iodide → 2-Bromo-1-methoxy-4-(methylsulfonyl)benzene
Reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:12].[C:13]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[O:12][CH3:13]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 2-bromo-4-(methylsulfonyl)phenol (3.2 g, 12.7 mmol) in DMF (35 mL) at 0° C. was added K2CO3 (5.3 g, 38.1 mmol). The reaction was stirred at 0° C. for 0.5 h and to this cold solution was slowly added CH3I (2.7 g, 19.1 mmol) drop wise. The reaction was stirred at r.t. overnight. After the reaction was completed, 80 mL of ice-water was added. The mixture was extracted with EA (60 mL×3). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and evaporation of the solvent, the obtained residue was purified on column chromatography (silica gel, ethyl acetate/petroleum ether=1:4) to give 2-bromo-1-methoxy-4-(methylsulfonyl)benzene (2.12 g, 63.0%) as yellow solid.
Workup
- stirringThe reaction was stirred at r.t. overnight
- extractionThe mixture was extracted with EA (60 mL×3)
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- filtrationAfter filtration and evaporation of the solvent
- customthe obtained residue was purified on column chromatography (silica gel, ethyl acetate/petroleum ether=1:4)
Sources & evidence
- ORD record
- ord-fe08088f57a5436691acbb38ad5bd9fd
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09150526B2
Reaction notes
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