Dimethyl Sulfate → 4-Iodo-2-nitroanisole

HRID 2378325Notes

Reaction equation

HRID 2378325 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]([O-])([O-])=O.[K+].[K+].COS(OC)(=O)=O>CC(C)=O>[CH3:12][O:1][C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 179373Phenol, 4-iodo-2-nitro-

Product 1

HCID 122498664-Iodo-2-nitroanisole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

4-Hydroxy-3-nitroiodobenzene (3.2 g, 12.0 mmol) was dissolved in acetone (30 mL). K2CO3 (1.8 g, 1.1 equiv) and Me2SO4 (1.23 mL, 1.1 equiv) were added to the solution. The mixture was stirred at 65° C. for 12 h. The reaction was then cooled, concentrated, and diluted with H2O (100 mL) and CHCl3 (100 mL). The mixture was shaken in a separatory funnel. The organic layer was dried (Na2SO4), filtered, and concentrated to afford 4-methoxy-3-nitroiodobenzene as a beige solid (3.3 g, 12.0 mmol, quant.): mp: 92-93° C. 1H NMR (300 M Hz, CDCl3) δ 8.13 (d, 1H, J=2.4 Hz), 7.81 (dd, 1H, J=8.7, 2.4 Hz), 6.86 (d, 1H, J=8.7 Hz), 3.95 (s, 3H).

Workup

  1. temperatureThe reaction was then cooled
  2. concentrationconcentrated
  3. additiondiluted with H2O (100 mL) and CHCl3 (100 mL)
  4. stirringThe mixture was shaken in a separatory funnel
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d3568f59cdb3428fba2bed692343f0b2
Source dataset
uspto-grants-2008_12
Patent number
US07470723B2

Reaction notes

Loading…