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

HRID 1110875Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1110875
[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

Quellen und Nachweise

ORD-Eintrag
ord-8e93d94968414fc6b7db7d8b031b10a1
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04977178

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