1,3,5-Tri-tert-butylbenzene → 1-Bromo-3,5-di-tert-butylbenzene

HRID 1017154

Reaktionsgleichung

Reaktionsgleichung von HRID 1017154
[C:1]([C:5]1[CH:10]=[C:9](C(C)(C)C)[CH:8]=[C:7]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:19]Br>C(Cl)(Cl)(Cl)Cl>[C:1]([C:5]1[CH:10]=[C:9]([Br:19])[CH:8]=[C:7]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

4

Edukt 2

HCID 150891,3,5-Tri-tert-butylbenzeneHCID 24408Bromine

Produkt 1

HCID 6201361-Bromo-3,5-di-tert-butylbenzeneAusbeute 61,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1,3,5-Tri-t-butylbenzene (150 g, 0.6 mol) was dissolved in 600 mL of carbon tetrachloride in a three-neck flask painted black to avoid light; The flask was equipped with an overhead stirrer, a thermometer, and an addition funnel under argon. Ferric chloride (3.0 g, 0.018 mol) was added and the solution was cooled to 0° C. A solution of bromine (120 g, 0.75 mol) dissolved in 200 mL of carbon tetrachloride was then added over a 2-hour period. The solution was stirred for an additional 1 hour at 0° C. and quenched with ice water. The layers were separated and the organics washed with 10% sodium hydroxide solution. The solution was then washed with salt brine and dried over magnesium sulfate. The solvent was removed under vacuum and the product was distilled through a 2-ft (60-cm) column under vacuum two times. The fractions boiling at 90°-110° C. at 0.4 mm Hg were combined and recrystallized from heptane to give 100 g of pure 3,5-di-t-butylbromobenzene (60% yield).

Aufarbeitung

  1. customThe flask was equipped with an overhead stirrer
  2. additionwas then added over a 2-hour period
  3. customquenched with ice water
  4. customThe layers were separated
  5. washthe organics washed with 10% sodium hydroxide solution
  6. washThe solution was then washed with salt brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed under vacuum
  9. distillationthe product was distilled through a 2-ft (60-cm) column under vacuum two times
  10. customrecrystallized from heptane

Quellen und Nachweise

ORD-Eintrag
ord-3a6222c2aa8d451d9cb45bff096f2da1
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06479424B1

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