Dimethyl Sulfate → 4-Bromoanisole

HRID 263073Notes

Reaction equation

HRID 263073 reaction equation
S([O:6][CH3:7])(OC)(=O)=O.[CH:8]1[C:13](O)=[CH:12][CH:11]=[C:10]([Br:15])[CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[Br:15][C:10]1[CH:11]=[CH:12][C:13]([O:6][CH3:7])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6497Dimethyl SulfateHCID 78084-BromophenolHCID 11430Potassium Carbonate

Product 1

HCID 77304-Bromoanisole

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

25 g (0.20 mol) of dimethyl sulphate are run over the course of 45 minutes into a refluxing suspension of 34.4 g (0.20 mol) of p-bromophenol and 27.5 g (0.20 mol) of potassium carbonate in 150 ml of acetone. The reflux is maintained for a further hour, the inorganic salts are removed by filtration and the filtrate is evaporated to dryness under reduced pressure. The residue is dissolved in diethyl ether, the ether solution is washed with dilute sodium hydroxide solution and water and is dried over dry sodium sulphate, and the solvent is evaporated to give 37.2 g of a slightly yellow oil which is insoluble in water.

Workup

  1. temperatureThe reflux is maintained for a further hour
  2. customthe inorganic salts are removed by filtration
  3. customthe filtrate is evaporated to dryness under reduced pressure
  4. dissolutionThe residue is dissolved in diethyl ether
  5. washthe ether solution is washed with dilute sodium hydroxide solution and water
  6. dry with materialis dried over dry sodium sulphate
  7. customthe solvent is evaporated
  8. customto give 37.2 g of a slightly yellow oil which

Sources & evidence

ORD record
ord-c143aa3bcf73492684d6e92640040e03
Source dataset
uspto-grants-1979_05
Patent number
US04156011

Reaction notes

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