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

HRID 1723557Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1723557
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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, pnmr/CDCl3 /delta/TMS

Quellen und Nachweise

ORD-Eintrag
ord-44a4e010abdd4a00a15a901d48962203
Quelldatensatz
uspto-grants-1989_08
Patentnummer
US04861880

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