Boron tribromide → 4-(4'-Hydroxyphenoxy)biphenyl

HRID 749936

Reaktionsgleichung

Reaktionsgleichung von HRID 749936
C[O:2][C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.O.ClCCl>ClCCl>[C:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:13][C:8]([O:7][C:6]2[CH:20]=[CH:21][C:3]([OH:2])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 25134Boron tribromideHCID 2668644-(4-Methoxyphenoxy)biphenylHCID 21908982Water methylene chloride

Produkt 1

HCID 105634264-(4'-Hydroxyphenoxy)biphenylAusbeute 50,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of the product from step 1 (0.5 g, 1.81 mmol) in dichloromethane (10 mL) at −78° C. was added boron tribromide (1.0 M solution in dichloromethane, 5.43 mL, 5.43 mmol) dropwise over 5-10 min. The subsequent mixture was stirred at −78° C. for an hour followed by ambient temperature for 1 h. After cooling the reaction mixture to 0° C., it was slowly added to cold water/dichloromethane (50 mL/50 mL). The organic portion was washed with water, brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel flash chromatography using hexane/EtOAc (gradient system) to give the title compound (0.24 g, 47%) as an off-white solid.

Aufarbeitung

  1. temperatureAfter cooling the reaction mixture to 0° C.
  2. washThe organic portion was washed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-217571d23617411da9d8bb5774b30b90
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402684B2

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