6-tert-Butyl-m-cresol → 4-Bromo-2-(tert-butyl)-5-methylphenol

HRID 1003850

Reaktionsgleichung

Reaktionsgleichung von HRID 1003850
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:6]=1[OH:12])([CH3:4])([CH3:3])[CH3:2].[Br:13]Br>C(Cl)(Cl)(Cl)Cl.O>[Br:13][C:9]1[C:8]([CH3:11])=[CH:7][C:6]([OH:12])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=1

Komponenten

5

Edukt 2

HCID 69376-tert-Butyl-m-cresolHCID 24408Bromine

Produkt 1

HCID 187986984-Bromo-2-(tert-butyl)-5-methylphenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 5943Carbon TetrachlorideLösungsmittel2×

Versuchsvorschrift

To a solution of 2-t-butyl-5-methylphenol (24.6 g, 150 mmol) in CCl4 (100 mL) at 0° C. was added a solution of bromine (7.7 mL, 150 mmol) in CCl4 (100 mL) over a 4 hour period. The mixture was stirred at room temperature for 30 minutes and then diluted with H2O. The organic phase was separated, washed with saturated sodium bisulfite and brine, and dried (MgSO4). Concentration gave a residue which was chromatographed on silica gel, eluting with 6:1 hexanes:EtOAc, to give the title compound. 1H NMR (CDCl3) δ 1.34 (s, 9 H), 2.24 (s, 3 H), 5.20 (s, 1 H), 6.54 (s, 1 H), 7.32 (s, 1 H).

Aufarbeitung

  1. customThe organic phase was separated
  2. washwashed with saturated sodium bisulfite and brine
  3. dry with materialdried (MgSO4)
  4. concentrationConcentration
  5. customgave a residue which
  6. customwas chromatographed on silica gel
  7. washeluting with 6:1 hexanes

Quellen und Nachweise

ORD-Eintrag
ord-1a3a65a5ceb44aa089a1c793dbecdc8e
Quelldatensatz
uspto-grants-2000_04
Patentnummer
US06046355

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