Water → 4'-Tert-butyl-2,5-dimethylbiphenyl-4-amine

HRID 1673189Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1673189
[C:1]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:15]1[C:21]([CH3:22])=[CH:20][C:18]([NH2:19])=[C:17]([CH3:23])[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>COCCOC.C1CCCCC1.C(OC(=O)C)C.C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:15]2[CH:16]=[C:17]([CH3:23])[C:18]([NH2:19])=[CH:20][C:21]=2[CH3:22])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

8

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27343204-tert-Butylphenylboronic acidHCID 81671304-Bromo-2,5-dimethylaniline

Produkt 1

HCID 598436854'-Tert-butyl-2,5-dimethylbiphenyl-4-amineAusbeute 72,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 1140TolueneLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittelHCID 21867204Cyclohexane ethylacetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

The reaction is carried out using inert conditions (argon or nitrogen atmosphere, dry solvents). A suspension of 6.4 g (36.0 mmol) of (4-tert-butylphenyl)boronic acid, 6.0 g (30.0 mmol) of 4-bromo-2,5-dimethylaniline, 29.3 g (90 mmol) caesium carbonate and 0.7 g (0.6 mmol) tetrakis(triphenylphosphin)palladium in 75 ml of 1,2-dimethoxyethan was stirred for 16 hrs at 80° C. At room temperature 25 ml of water and 75 ml of toluene were added. The organic layer was separated, the watery layer was again extracted using 75 ml of toluene. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Column chromatographic (cyclohexane/ethylacetate:2/1) yielded 5.5 g (21.7 mmol) 72% of 4′-tert-butyl-2,5-dimethylbiphenyl-4-amine (log P (pH 2.3)=3.65.

Aufarbeitung

  1. customThe organic layer was separated
  2. extractionthe watery layer was again extracted
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a785811753f444e9903adc4db75da154
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07999137B2

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