Dimethyl Sulfate → 4-Bromo-2-chloro-6-methylanisole

HRID 1110875Notes

Reaction equation

HRID 1110875 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([OH:9])=[C:4]([Cl:10])[CH:3]=1.[C:11]([O-])([O-])=O.[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([O:9][CH3:11])=[C:4]([Cl:10])[CH:3]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 820314-Bromo-6-chloro-o-cresol

Product 1

HCID 30218344-Bromo-2-chloro-6-methylanisole

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Bromo-2-chloro-6-methylphenol (50 g, 0.225 mole) and K2CO3 (31.8 g, 0.23 mole) were combined in acetone (300 ml). Dimethyl sulfate (32 ml, 0.34 mole) was added dropwise and the mixture stirred 22 hours at room temperature, filtered and concentrated to an oil in vacuo. The oil was taken up in 250 ml ether, washed 2×2N NaOH, 1×saturated NaHCO3, 2×brine, dried over MgSO4, reconcentrated to an oil and distilled to yield purified title product, 42.9 g, b.p. 122°-124°0.9 mm, pnmr/CDCl3 /delta/TMS: 2.3 (s, 3H), 3.8 (s, 3H), 7.3 (q, 2H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated to an oil in vacuo
  3. washwashed 2×2N NaOH, 1×saturated NaHCO3, 2×brine
  4. dry with materialdried over MgSO4
  5. distillationdistilled
  6. customto yield
  7. custompurified title product, 42.9 g, b.p. 122°-124°0.9 mm

Sources & evidence

ORD record
ord-8e93d94968414fc6b7db7d8b031b10a1
Source dataset
uspto-grants-1990_12
Patent number
US04977178

Reaction notes

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