1,2-Dimethoxyethane → 2-Cyano-4'-methylbiphenyl

HRID 1937098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1937098
[Li+].[Cl-].C(COC)OC.Br[C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]#[N:13].[C:18]1([CH3:26])[CH:23]=[CH:22][C:21]([Mg]Cl)=[CH:20][CH:19]=1>O1CCCC1.Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]1([CH3:26])[CH:23]=[CH:22][C:21]([C:10]2[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=2[C:12]#[N:13])=[CH:20][CH:19]=1

Komponenten

7

Edukt 4

HCID 80711,2-DimethoxyethaneHCID 162722-BromobenzonitrileHCID 433294Lithium ChlorideHCID 178426149HCID 178426149, Verbindung

Produkt 1

HCID 1455122-Cyano-4'-methylbiphenyl

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11017392(1,3-Bis(diphenylphosphino)propane)palladium(II) chlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A suspension of MnCl2 (0.25 g, 1.98 mmol) and LiCl (0.17 g, 3.955 mmol) in a mixture of 2 ml of anhydrous tetrahydrofuran and 0.38 ml of dimethoxyethane (3.955 mmol) is stirred at room temperature. After stirring for approximately 30 minutes, a homogeneous medium is obtained. The addition is then so carried out of 1/1: PdCl2/dppp (0.023 g, 1 mol %) and of o-bromobenzonitrile (0.72 g, 3.955 mmol) and then a solution of p-tolylmagnesium chloride in tetrahydrofuran (1.80N, 2.86 ml, 5.14 mmol) is added over 2 hours at room temperature. After stirring for 90 minutes, the reaction mixture is treated as described in Example 1. The o-(p-tolyl)benzonitrile is thus obtained with a yield of isolated product of 95%.

Aufarbeitung

  1. stirringAfter stirring for approximately 30 minutes
  2. customa homogeneous medium is obtained
  3. additionThe addition
  4. stirringAfter stirring for 90 minutes
  5. additionthe reaction mixture is treated

Quellen und Nachweise

ORD-Eintrag
ord-5acca62d383e459c9c27e18d69ca5c74
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06392080B1

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