Water → 4-(4'-Hydroxyphenoxy)biphenyl

HRID 749995Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 749995
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.O>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

4

Edukt 2

HCID 962WaterHCID 2668644-(4-Methoxyphenoxy)biphenyl

Produkt 1

HCID 105634264-(4'-Hydroxyphenoxy)biphenylAusbeute 12,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a solution of 4-(4-methoxy-phenoxy)-biphenyl (3.2 g, 11.6 mmol) in anhydrous dichloromethane (60 mL) at −78° C. was added borontribromide (1M solution in dichloromethane) (7.52 g, 30 mmol) over a period of 15 min. The reaction mixture was stirred at −78° C. for 1 h, warmed to rt and stirred at rt for 1 h. The mixture was cooled to 0-5° C. Cold water (125 mL) was added over a period of 10 min and the mixture was extracted with dichloromethane (250 mL). The organic layer was dried over anhydrous Na2SO4. The crude mixture was purified by silica gel flash chromatography to obtain the title product (375 mg, 12%).

Aufarbeitung

  1. temperaturewarmed to rt
  2. stirringstirred at rt for 1 h
  3. temperatureThe mixture was cooled to 0-5° C
  4. extractionthe mixture was extracted with dichloromethane (250 mL)
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. customThe crude mixture was purified by silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0b034bfd63064aef8717dfd5c1426639
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07402684B2

Notizen zur Reaktion

Wird geladen…