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

HRID 1061485

Reaktionsgleichung

Reaktionsgleichung von HRID 1061485
[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.[Fe].C(C1C=CC=C(O)C=1O)(C)(C)C>[Br:19][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:6]=[C:7]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:8]=1

Komponenten

6

Edukt 2

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

Produkt 1

HCID 6201361-Bromo-3,5-di-tert-butylbenzeneAusbeute 46,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 77643tert-ButylcatecholKatalysatorHCID 5943Carbon TetrachlorideLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

1,3,5-Tri-t-butylbenzene (150 g, 0.6 mol) was dissolved in carbon tetrachloride (300 mL) in a three-necked flask which had been painted black to avoid light and equipped with an overhead stirrer, thermometer and addition funnel under argon. Iron pellets (36 g, 0.64 mol) were added and the slurry was cooled to 5° C. t-Butylcatechol (1.0 g) was added and a solution of bromine (201.6 g, 1.26 mol) in carbon tetrachloride (75 mL) was added over a one hour period. The slurry was stirred for an additional 4 hours at 5° C. and quenched by pouring into 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 evaporated and the product was distilled under vacuum twice to give 75 g of product which was then recrystallized from heptane to give 47 g of pure product (29%).

Aufarbeitung

  1. customequipped with an overhead stirrer
  2. additionthermometer and addition funnel under argon
  3. additionwere added
  4. additionwas added
  5. customquenched
  6. additionby pouring into ice water
  7. customThe layers were separated
  8. washthe organics washed with 10% sodium hydroxide solution
  9. washThe solution was then washed with salt brine
  10. dry with materialdried over magnesium sulfate
  11. customThe solvent was evaporated
  12. distillationthe product was distilled under vacuum twice

Quellen und Nachweise

ORD-Eintrag
ord-a808ca913520497babcc3d8b4fd76010
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06960550B2

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