Methyl iodide → 1-Bromo-4-methoxy-2-methyl-3-nitrobenzene
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH3:12].[C:13]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:13][O:8][C:5]1[CH:6]=[CH:7][C:2]([Br:1])=[C:3]([CH3:12])[C:4]=1[N+:9]([O-:11])=[O:10]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
4-Bromo-3-methyl-2-nitrophenol (7.17 g, 31 mmol, Intermediate 41) was dissolved in acetone (50 mL). K2CO3 (8.65 g, 62 mmol) was added, followed by MeI (3.9 mL, 62 mmol) and the reaction mixture was stirred at ambient temperature for 18 hrs. The crude mixture was concentrated, H2O was added and the mixture was extracted with CH2Cl2, dried over Na2SO4, filtered and evaporated to give 4-bromo-3-methyl-2-nitrophenyl methyl ether, 7 g (92%).
Workup
- concentrationThe crude mixture was concentrated
- additionH2O was added
- extractionthe mixture was extracted with CH2Cl2
- dry with materialdried over Na2SO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-c460060cc2a44828a5fa4e0406bb1a7d
- Source dataset
- uspto-grants-2010_10
- Patent number
- US07812017B2
Reaction notes
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