Stannane, trimethyl(4-methylphenyl)- → 2-Cyano-4'-methyl-4-nitrobiphenyl

HRID 1729449

Reaktionsgleichung

Reaktionsgleichung von HRID 1729449
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([Sn](C)(C)C)=[CH:3][CH:2]=1.Br[C:13]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:14]=1[C:15]#[N:16]>C1(C)C=CC=CC=1.CCOC(C)=O.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>[C:15]([C:14]1[CH:17]=[C:18]([N+:21]([O-:23])=[O:22])[CH:19]=[CH:20][C:13]=1[C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)#[N:16]

Komponenten

6

Edukt 2

HCID 617834Stannane, trimethyl(4-methylphenyl)-HCID 70954232-Bromo-5-nitrobenzonitrile

Produkt 1

HCID 190122062-Cyano-4'-methyl-4-nitrobiphenylAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of p-tolyltrimethyltin (389 mg, 1.525 retool) in dry toluene (5 mL) under N2 was added 2-bromo-5-ni tro-benzonitrile (276 mg, 1.22 mmol) and Pd(PPh3)4 (176 mg; 10 mol %). The reaction was stirred at reflux under N2 for 24 hours and then cooled to room temperature. The mixture was diluted with EtOAc and the solid was removed by filtration through a pad of celite. The liltrate was concentrated in vacuo and the residue was purified by flash chromatography on a silica column eluting with Hex/EtOAc (10:1) to afford 214 mg (74%) of the titled compound as a slightly yellow solid. 1H NMR (300 MMz, CDCl3) δ 2.42 (s, 3H), 7.32 (d, 2H), 7.48 (d, 2H), 7.69 (d, 1H), 8.45 (dd, 1H), 8.61 (s, 1H).

Aufarbeitung

  1. temperatureat reflux under N2 for 24 hours
  2. customthe solid was removed by filtration through a pad of celite
  3. concentrationThe liltrate was concentrated in vacuo
  4. customthe residue was purified by flash chromatography on a silica column
  5. washeluting with Hex/EtOAc (10:1)

Quellen und Nachweise

ORD-Eintrag
ord-17d68daed44e47689303f3c6fa0c53da
Quelldatensatz
uspto-grants-1994_07
Patentnummer
US05332744

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