Dimethyl Sulfate → 1-Bromo-3-tert-butyl-5-iodo-2-methoxybenzene

HRID 403666Notes

Reaction equation

HRID 403666 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([C:9]([CH3:12])([CH3:11])[CH3:10])[C:3]=1[OH:13].[C:14](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O>CC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([C:9]([CH3:10])([CH3:12])[CH3:11])[C:3]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 123362192-Bromo-6-tert-butyl-4-iodophenol

Product 1

HCID 667000451-Bromo-3-tert-butyl-5-iodo-2-methoxybenzene

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 2-bromo-6-tert-butyl-4-iodophenol (5.0 g, 14.08 mmol) in acetone (50 mL) was treated with potassium carbonate (2.92 g, 21.13 mmol) and dimethylsulfate (1.95 g, 15.49 mmol) at reflux for 16 hours, cooled and concentrated. The residue was dissolved in ethyl acetate, washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified on an Isco 40 g silica cartridge eluting with 2% ethyl acetate in hexane to give the title compound.

Workup

  1. temperatureat reflux for 16 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified on an Isco 40 g silica cartridge
  10. washeluting with 2% ethyl acetate in hexane

Sources & evidence

ORD record
ord-23e3c48b49ab4c73be74f1ebf34a802a
Source dataset
uspto-grants-2014_06
Patent number
US08748443B2

Reaction notes

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