2-Bromo-6-nitrotoluene → 2-Methyl-3-nitro-1,1'-biphenyl

HRID 846033

Reaktionsgleichung

Reaktionsgleichung von HRID 846033
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=1[CH3:11]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:2]1([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-:10])=[O:9])[C:3]=2[CH3:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

3

Edukt 1

HCID 1235372-Bromo-6-nitrotoluene

Produkt 1

HCID 105846962-Methyl-3-nitro-1,1'-biphenylAusbeute 120,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, VerbindungKatalysator

Versuchsvorschrift

A 100 mL round bottomed flask under argon was charged with 480 mg of tetrakis(triphenylphosphine)palladium(0), and 3 g of 2-bromo-6-nitrotoluene dissolved in 50 mL of degassed, toluene. To this was added under argon 9 mL of a 2M degassed Na2CO3 aqueous solution, and then 1.7 g of phenylboronic acid dissolved in 20 mL of ethanol was added. The mixture was refluxed for 6 h with stirring. Residual boronic acid was removed by treatment with 30% H2O2 for 1 hour. The mixture was extracted with methylene chloride, washed with saturated brine, the combined organic extracts were dried over anhydrous magnesium sulfate, filtered and the solvent removed. The residue was chromatographed over silica gel using methylene chloride as the eluent to give 1.78 g (60% yield) of brownish crystals.

Aufarbeitung

  1. dissolutiondissolved in 50 mL
  2. customof degassed
  3. additionTo this was added under argon 9 mL of a 2M
  4. customdegassed Na2CO3 aqueous solution
  5. dissolution1.7 g of phenylboronic acid dissolved in 20 mL of ethanol
  6. additionwas added
  7. temperatureThe mixture was refluxed for 6 h
  8. customResidual boronic acid was removed by treatment with 30% H2O2 for 1 hour
  9. extractionThe mixture was extracted with methylene chloride
  10. washwashed with saturated brine
  11. dry with materialthe combined organic extracts were dried over anhydrous magnesium sulfate
  12. filtrationfiltered
  13. customthe solvent removed
  14. customThe residue was chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5f9e60c1b1bb4b0795ec4d9b01baa551
Quelldatensatz
uspto-grants-1992_08
Patentnummer
US05135838

Verknüpfte Notizen

Wird geladen…