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

HRID 513229Notes

Reaction equation

HRID 513229 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[OH:11].[C:12]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[O:11][CH3:12]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 135454532-Bromo-6-nitrophenol

Product 1

HCID 225057131-Bromo-2-methoxy-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-Bromo-6-nitro-phenol (43.6 g, 0.2 mol), K2CO3 (82.9 g, 0.6 mol), acetone (600 mL) is stirred at 70° C. for 1 h. Then MeI (85.14 g, 0.6 mol) is slowly added to the reaction mixture and refluxed for 8 h. After reaction, filtered and the filtrate is extracted with ethyl acetate (3×1000 mL). The combined SnCl2 organic phase is washed with water and brine, dried over Na2SO4, concentrated in vacuo to obtain the desired product.

Workup

  1. temperaturerefluxed for 8 h
  2. customAfter reaction
  3. filtrationfiltered
  4. extractionthe filtrate is extracted with ethyl acetate (3×1000 mL)
  5. washThe combined SnCl2 organic phase is washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fc21f8157e4c4316b1787911eafff502
Source dataset
uspto-grants-2015_08
Patent number
US09102684B2

Reaction notes

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