Propylene Oxide → 2-Bromo-5-tert-butyl-1,3-dimethylbenzene

HRID 867981

Reaktionsgleichung

Reaktionsgleichung von HRID 867981
[C:1]([C:5]1[CH:6]=[C:7]([CH3:12])[CH:8]=[C:9]([CH3:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C1OC1C.[Br:17]Br.[OH-].[K+]>C(Cl)Cl.O>[Br:17][C:8]1[C:7]([CH3:12])=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][C:9]=1[CH3:11]

Komponenten

7

Edukt 4

HCID 6378Propylene OxideHCID 73785-Tert-butyl-m-xyleneHCID 14797Potassium HydroxideHCID 24408Bromine

Produkt 1

HCID 2203642-Bromo-5-tert-butyl-1,3-dimethylbenzeneAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 200 g (1.23 mole) 5-t-butyl-1,3-dimethylbenzene and 83 ml (1.23 mole) propylene oxide in 500 ml of methylene chloride at 15° C. or less, 63 ml (1.23 mole) bromine was added dropwise while maintaining the solution temperature at 15° C. or less. The reaction mixture was allowed to warm to 25° C. overnight. A 200 ml solution of 5% by weight of potassium hydroxide in water was added and the resulting two phase system was stirred for 1 hr at 25° C. The organic phase was washed with water and dried over anhydrous magnesium sulfate. After solvent evaporation an oil was left which when crystallized from methanol gave 265 g (87% yield) of the title compound after drying in vacuo. The oil could also be purified by distilling at 61°-70° C. under a reduced pressure of 0.25 mm of mercury.

Aufarbeitung

  1. temperaturewhile maintaining the solution temperature at 15° C. or less
  2. washThe organic phase was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter solvent evaporation an oil
  5. waitwas left which when
  6. customcrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-738fe73501f0484cb7b8643d628aeb3a
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04777270

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