Dimethyl Sulfate → 4-Bromo-2-chloroanisole

HRID 1839927Notes

Reaction equation

HRID 1839927 reaction equation
COS([O:6][CH3:7])(=O)=O.[Br:8][C:9]1[CH:14]=[CH:13][C:12](O)=[C:11]([Cl:16])[CH:10]=1.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([O:6][CH3:7])=[C:11]([Cl:16])[CH:10]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 198594-Bromo-2-chlorophenol

Product 1

HCID 30165374-Bromo-2-chloroanisoleYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Under nitrogen, 7.3 mL (77 mmol) of dimethylsulfate was added to a stirred suspension of 10 g (48 mmol) of 4-bromo-2-chlorophenol and 5.4 g (38 mmol) of powered K2CO3 in 75 mL of fresh acetone. After 2 hours at reflux, the reaction was cooled to ambient temperature, filtered, and concentrated in vacuo. The residue was dissolved in ethyl acetate; the resulting solution was washed with water and dried over MgSO4. Concentration in vacuo gave 10.2 g (96%) of 4-bromo-2-chloroanisole as a colorless solid: mp 68.5-70.5° C.; NMR (CDCl3) δ 3.88 (s, 3H), 6.80 (d, J=9 Hz, 1H), 7.33 (dd, J=2, 9 Hz, 1H), 7.50 (d, J=2 Hz, 1H).

Workup

  1. temperatureAfter 2 hours at reflux
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washthe resulting solution was washed with water
  6. dry with materialdried over MgSO4
  7. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-3be01a0e42ea40d8aceed25133ef0db4
Source dataset
uspto-grants-2004_01
Patent number
US06677488B2

Reaction notes

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