Methyl iodide → 1-Bromo-4-methoxy-2-methyl-3-nitrobenzene

HRID 1159791Notes

Reaction equation

HRID 1159791 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

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 130881794-Bromo-3-methyl-2-nitrophenol2×

Product 1

HCID 113570121-Bromo-4-methoxy-2-methyl-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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

  1. concentrationThe crude mixture was concentrated
  2. additionH2O was added
  3. extractionthe mixture was extracted with CH2Cl2
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c460060cc2a44828a5fa4e0406bb1a7d
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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