Sodium Carbonate → HCID 67254694, Verbindung

HRID 536617Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 536617
Br[C:2]1[C:6]([Br:7])=[CH:5][S:4][CH:3]=1.[CH3:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1B1OC(C)(C)C(C)(C)O1)[C:12]#[N:13].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.O.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>[Br:7][C:6]1[C:2]([C:16]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][C:9]=2[CH3:8])=[CH:3][S:4][CH:5]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 184523,4-DibromothiopheneHCID 567769293-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Produkt 1

HCID 67254694HCID 67254694, VerbindungAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 86587398Ethanol toluene waterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3,4-dibromothiophene (3 g, 12.5 mmol), 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (2 g, 12.5 mmol), Na2CO3 (2.7 g, 25 mmol), Pd(PPh3)4 (1.4 g, 1.25 mmol) in a mixture of toluene/EtOH/H2O (40 mL, 5:3:2) was stirred at 80° C. under nitrogen overnight. The reaction mixture was diluted with EtOAc (80 mL), and washed with water and brine. The organic phase was dried over Na2SO4, concentrated in vacuo, and purified on silica gel column (PE: EtOAc=30:1) to afford 4-(4-bromothiophen-3-yl)-3-methylbenzonitrile (Scheme III, 13, X1=4-cyano-2-methylphenyl) (2.4 g, yield 68%) as yellow oil. 1H NMR (CD3OD 400 MHz): δ 7.56 (s, 1H), 7.50-7.48 (m, 2H), 7.31 (d, J=3.2 Hz, 1H), 7.22 (d, J=7.6 Hz, 1H), 2.10 (s, 3H).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. custompurified on silica gel column (PE: EtOAc=30:1)

Quellen und Nachweise

ORD-Eintrag
ord-3eacde70836241928a06b88412f43348
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859611B2

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