Boron tribromide → 4-Cyclohexyl-3-isopropyl-phenol

HRID 237819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 237819
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([O:13]C)=[CH:9][C:8]=2[CH:15]([CH3:17])[CH3:16])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B(Br)(Br)Br>C(Cl)Cl>[CH:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=2[CH:15]([CH3:17])[CH3:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 68529356Cyclohexyl-4-methoxy-2-isopropyl-benzene

Produkt 1

HCID 685276534-Cyclohexyl-3-isopropyl-phenolAusbeute 120,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To 1-cyclohexyl-4-methoxy-2-isopropyl-benzene (2.09 g, 9.0 mmol) in CH2Cl2 (20 mL) was added BBr3 (1 M in CH2Cl2, 22.5 mmol) dropwise at 0° C. This mixture was stirred at 0° C. for two hours. The reaction mixture was then quenched with MeOH (5 mL), after which aqueous sodium hydrogen carbonate (10 mL) was added. The reaction mixture was stirred at room temperature for one hour and extracted with CH2Cl2 three times. The organic phase was washed with brine, dried (Na2SO4) and concentrated. Silica gel chromatography (0-2% EtOAc/heptane) provided 2.36 g of the title compound.

Aufarbeitung

  1. customThe reaction mixture was then quenched with MeOH (5 mL)
  2. additionafter which aqueous sodium hydrogen carbonate (10 mL) was added
  3. stirringThe reaction mixture was stirred at room temperature for one hour
  4. extractionextracted with CH2Cl2 three times
  5. washThe organic phase was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-660d62a3883840528717127d539e9152
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642603B2

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