Potassium Carbonate → 4-Chloro-3-methyl-1,1'-biphenyl

HRID 1883629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1883629
Br[C:2]1[CH:3]=[CH:4][C:5]([Cl:9])=[C:6]([CH3:8])[CH:7]=1.OB(O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[Cl:9][C:5]1[CH:4]=[CH:3][C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][C:6]=1[CH3:8]

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 6098995-Bromo-2-chlorotoluene

Produkt 1

HCID 203296724-Chloro-3-methyl-1,1'-biphenylAusbeute 79,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 5.00 g (24.3 mmol) of 5-bromo-2-chlorotoluene, 3.56 g (29.2 mmol) of dihydroxyphenylborane, 546 mg (2.43 mmol) of palladium acetate (II), 9.41 g (29.2 mmol) of tetrabutylammonium bromide, 8.40 g (60.8 mmol) of potassium carbonate and 50 ml of water was stirred for 5 hours at 80° C. under nitrogen flow. The reaction solution was filtrated through celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, then, concentrated. The residue was subjected to silica gel column chromatography (eluant: hexane) to obtain 3.92 g of 4-chloro-3-methylbiphenyl.

Aufarbeitung

  1. filtrationThe reaction solution was filtrated through celite
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-39d0017a820b43ab90ec63575e3da0ca
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06762197B2

Notizen zur Reaktion

Wird geladen…