Cesium carbonate → 2-Isobutyl-5-nitrobenzonitrile

HRID 1942629

Reaktionsgleichung

Reaktionsgleichung von HRID 1942629
[CH2:1](B(O)O)[CH:2]([CH3:4])[CH3:3].Br[C:9]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:10]=1[C:11]#[N:12].C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:3][CH:2]([CH3:4])[CH2:1][C:9]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:10]=1[C:11]#[N:12]

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 2734395(2-Methylpropyl)boronic acidHCID 70954232-Bromo-5-nitrobenzonitrile

Produkt 1

HCID 222280302-Isobutyl-5-nitrobenzonitrileAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418807HCID 178418807, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of isobutylboronic acid (5.89 g), 2-bromo-5-nitrobenzo nitrile (12.5 g) and Cs2CO3 (35.9 g) in toluene (150 mL) and water (5 mL) stirred under nitrogen at room temperature was added solid PdCl2(dppf)-CH2Cl2 adduct (2.248 g) in one charge. The reaction mixture was stirred at 100° C. for 16 h. After cooling the reaction, the solvent was removed in vacuo. The residue was purified by column chromatography to give 2-(2-methylpropyl)-5-nitrobenzonitrile (D56) (11 g) as a light yellow oil. δH (CDCl3, 400 MHz): 1.00 (6H, d), 2.06 (1H, m), 2.86 (2H, d), 7.52 (1H, d), 8.37 (1H, dd), 8.51 (1H, d).

Aufarbeitung

  1. additioncharge
  2. temperatureAfter cooling
  3. customthe reaction
  4. customthe solvent was removed in vacuo
  5. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5370d3e5a82a4786bfd2d3dd6922fec6
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389508B2

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