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

HRID 2278394Notes

Reaction equation

HRID 2278394 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+].IC>CC(C)=O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:13])=[C:4]([N+:9]([O-:11])=[O:10])[C:3]=1[CH3:12]

Participants

5

Reactant 3

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

Product 1

HCID 113570121-Bromo-4-methoxy-2-methyl-3-nitrobenzeneYield 96.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 4-bromo-3-methyl-2-nitro-phenol (30 g, 0.13 mol) in acetone (200 mL) was added K2CO3 (39 g, 0.28 mol) and iodomethane (17.6 mL, 0.28 mol). The mixture was stirred for 18 hrs and then it was concentrated, diluted with water and extracted with CH2Cl2. The organic phase was dried over Na2SO4, filtered and concentrated to give 1-bromo-4-methoxy-2-methyl-3-nitro-benzene (31 g, 96%) which was used without further purification.

Workup

  1. concentrationit was concentrated
  2. additiondiluted with water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8bc4005425134cb59ba05a16151b6962
Source dataset
uspto-grants-2015_09
Patent number
US09133180B2

Reaction notes

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