4-Bromo-o-xylene → Biphenyl

HRID 255471

Reaktionsgleichung

Reaktionsgleichung von HRID 255471
Br[C:2]1[CH:3]=[C:4]([CH3:9])[C:5](C)=[CH:6][CH:7]=1.[Mg]>O1CCCC1.[Cu](Cl)Cl>[C:9]1([C:4]2[CH:3]=[CH:2][CH:7]=[CH:6][CH:5]=2)[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1

Komponenten

5

Edukt 2

HCID 685044-Bromo-o-xyleneHCID 5462224Magnesium

Produkt 1

HCID 7095BiphenylAusbeute 50,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24014Cupric ChlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 13.7 g of 4-bromo-o-xylene in 50 ml of dry tetrahydrofuran is added dropwise to a suspension of magnesium filings (1.95 g) in 50 ml of dry tetrahydrofuran in the course of 1 hour. After refluxing in an argon atmosphere for 2 hours, the mixture is cooled to room temperature and 9.4 g of anhydrous copper(II) chloride are added in portions. The mixture is poured onto ice-water and extracted twice with 100 ml of diethyl ether each time. The organic phase is washed with 2 N hydrochloric acid and saturated sodium chloride solution. Drying with magnesium sulfate, evaporation and crystallisation of the residue from ethanol gives 2.9 g of biphenyl.

Aufarbeitung

  1. temperatureAfter refluxing in an argon atmosphere for 2 hours
  2. additionThe mixture is poured onto ice-water
  3. extractionextracted twice with 100 ml of diethyl ether each time
  4. washThe organic phase is washed with 2 N hydrochloric acid and saturated sodium chloride solution
  5. dry with materialDrying with magnesium sulfate, evaporation and crystallisation of the residue from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-74a2fe7f25f648818b8b50004d6cbf57
Quelldatensatz
uspto-grants-1987_10
Patentnummer
US04698295

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