Sulfuric Acid → 4-Bromo-2-tert-butylphenol

HRID 377342

Reaktionsgleichung

Reaktionsgleichung von HRID 377342
Br[C:2]1[CH:3]=[CH:4][C:5]([C:9]([CH3:12])([CH3:11])[CH3:10])=[C:6]([OH:8])[CH:7]=1.[Br:13]C1C=CC(O)=CC=1.C(O)(C)(C)C.S(=O)(=O)(O)O>C(Cl)(Cl)(Cl)Cl>[Br:13][C:3]1[CH:2]=[CH:7][C:6]([OH:8])=[C:5]([C:9]([CH3:12])([CH3:11])[CH3:10])[CH:4]=1

Komponenten

6

Edukt 4

HCID 1118Sulfuric Acid2×HCID 6386tert-ButanolHCID 78084-BromophenolHCID 103313825-Bromo-2-tert-butylphenol2×

Produkt 1

HCID 970684-Bromo-2-tert-butylphenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 5943Carbon TetrachlorideLösungsmittel

Versuchsvorschrift

Using the same procedure as for the preparation of 5-bromo-2-t-butylphenol (Compound D), but instead using 50 g (289.0 mmol) of 4-bromophenol, 21.40 g (27.25 ml, 289.0 mmol) of t-butanol and 14 ml of conc. sulfuric acid (added slowly) and 140 ml of distilled carbon tetrachloride, stirred at room temperature for 24 hours produced a dull green-colored solution and a white precipitate. At this time an additional 3.5 ml of conc. sulfuric acid was added and the solution was allowed to stir for 4 days more at room temperature. After aqueous workup, a dark yellow oil was isolated. Purification by flash chromatography (silica, 2% ethyl acetate in hexane) yielded the title compound as a clear, light yellow oil. PMR (CDCl3): d 1.38 (9H, s), 4.79 (1H, s), 6.54 (1H, d, J=8.5 Hz), 7.16 (1H, dd, J=8.5, 2.5 Hz), 7.35 (1H, d, J=2.5 Hz).

Aufarbeitung

  1. customproduced a dull green-colored solution
  2. stirringto stir for 4 days more at room temperature
  3. customAfter aqueous workup, a dark yellow oil was isolated
  4. customPurification by flash chromatography (silica, 2% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-7061dec1a06d4ed09bdc8fb6306270b7
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06025388

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