Hexane → 2',4',6'-Trimethyl-3-nitro-biphenyl-2-carboxylic acid methyl ester

HRID 377045

Reaktionsgleichung

Reaktionsgleichung von HRID 377045
Br[C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:3]=1[C:4](OC)=O.[F-].[Cs+].[C:17]1([CH3:28])[CH:22]=[C:21](C)[CH:20]=[C:19]([CH3:24])[C:18]=1B(O)O.CCCCCC.[C:35]([O:38][CH2:39]C)(=[O:37])C>C(COC)OC.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>[CH3:39][O:38][C:35]([C:8]1[C:3]([C:4]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:24])=[CH:18][C:17]=2[CH3:28])=[CH:2][CH:11]=[CH:10][C:9]=1[N+:12]([O-:14])=[O:13])=[O:37]

Komponenten

8

Edukt 5

HCID 8058HexaneHCID 8857Ethyl AcetateHCID 25953Cesium fluorideHCID 245494Methyl 2-Bromo-5-nitrobenzoateHCID 2921842,4,6-Trimethylbenzeneboronic acid

Produkt 1

HCID 538563352',4',6'-Trimethyl-3-nitro-biphenyl-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere in 20 ml of anhydrous dimethoxyethane (DME) was combined 1.44 g (5.54 mmol) of methyl 2-bromo-5-nitrobenzoate 1.68 g (11.1 mmol) of cesium fluoride and 192 mg of tetrakis(triphenylphosphine)palladium(0). The reaction was stirred for 5 minutes, at which point 1.00 g (6.09) of mesitylboronic acid was added. The solution was heated to reflux for 20 hours, and was then cooled and fractionated on silica gel using 6:1 hexane: ethyl acetate (EtOAc) to afford, after concentration in vacuo and refractionation using toluene, 5.65 g (54%) of the title compound.

Aufarbeitung

  1. additionwas added
  2. temperatureThe solution was heated
  3. temperatureto reflux for 20 hours
  4. temperaturewas then cooled
  5. concentrationafter concentration in vacuo and refractionation

Quellen und Nachweise

ORD-Eintrag
ord-43ad98a996a64243884dad4eee8f09b5
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06022978

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