2,6-Di-tert-butylphenol → 4-Bromo-2,6-di-tert-butylphenol

HRID 399326

Reaktionsgleichung

Reaktionsgleichung von HRID 399326
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[Br:16]Cl>C(Cl)CCl.CCOCC>[Br:16][C:9]1[CH:10]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]([OH:15])=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=1

Komponenten

5

Edukt 2

HCID 314052,6-Di-tert-butylphenolHCID 61697BROMINE CHLORIDE (BrCl)

Produkt 1

HCID 708294-Bromo-2,6-di-tert-butylphenolAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a solution of 2,6-di-tert-butylphenol (2.06 g, 10 mmol) in EDC (50 mL) in a 200-mL round bottom flask, was added the stabilized BrCl brominating reagent (12 mL, about 11 mmol) dropwise, with stirring at room temperature. Initially, the orange reddish color of the reagent disappeared quickly. The color from the last 1 mL persisted for several minutes. The reaction mixture was allowed to stand for 30 minutes before being quenched with a few drops of sodium sulfite solution. After phase separation, it was diluted with EDC (50 mL), washed with water (100 mL) and dried (Na2SO4). The organic layer was concentrated under reduced pressure to afford a glue-like material. The material was redissolved in ether (10 mL) and after solvent removal, a crystalline solid 4-bromo-2,6-di-tert-butylphenol product (2.63 g, 92% recovered yield) was obtained in high purity (>98% by GC).

Aufarbeitung

  1. waitThe color from the last 1 mL persisted for several minutes
  2. custombefore being quenched with a few drops of sodium sulfite solution
  3. customAfter phase separation, it
  4. additionwas diluted with EDC (50 mL)
  5. washwashed with water (100 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationThe organic layer was concentrated under reduced pressure
  8. customto afford a glue-like material
  9. customafter solvent removal

Quellen und Nachweise

ORD-Eintrag
ord-f83b1b5df26c4f0489d308504a235b0f
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05817888

Verknüpfte Notizen

Wird geladen…