4-Chlorotoluene → 4-Methylbiphenyl

HRID 227864

Reaktionsgleichung

Reaktionsgleichung von HRID 227864
C(P(C(C)(C)C)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C)(C)C.[OH-].[OH-].[C:24]1([B+2])C=CC=CC=1.ClC1C=CC(C)=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:24][C:15]1[CH:14]=[CH:13][C:12]([C:7]2[CH:6]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 78104-ChlorotolueneHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 178419127HCID 178419127, Verbindung

Produkt 1

HCID 125664-Methylbiphenyl

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Versuchsvorschrift

An oven dried resealable Schlenk tube was evacuated and backfilled with argon and charged with palladium acetate (2.2 mg, 0.01 mmol, 1.0 mol %), 2-(di-tert-butylphosphino)biphenyl (4.5 mg, 0.015 mmol, 1.5 mol %), phenylboron dihydroxide (183 mg, 1.5 mmol), additive (3.0 mmol), and 4-chlorotoluene (0.12 mL, 1.0 mmol). The tube was evacuated and backfilled with argon, and THF (2 mL) was added through a rubber septum. The reaction mixture was stirred at room temperature for 20 hours. The reaction mixture was then diluted with ethyl acetate (30 mL) and poured into a separatory funnel. The mixture was washed with 2.0M NaOH (20 mL), followed by brine (20 mL). The organic layer was submitted for GC analysis giving the results tabulated below.

Aufarbeitung

  1. customAn oven dried resealable Schlenk tube
  2. customwas evacuated
  3. customThe tube was evacuated
  4. additionwas added through a rubber septum
  5. additionThe reaction mixture was then diluted with ethyl acetate (30 mL)
  6. additionpoured into a separatory funnel
  7. washThe mixture was washed with 2.0M NaOH (20 mL)
  8. customgiving the results

Quellen und Nachweise

ORD-Eintrag
ord-f6158e24870b494ca233a54b9fc4989e
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560582B2

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