Sodium Carbonate → 4,5-Bis(4-chloro-2-methylphenyl)thiophene-2-carbonitrile

HRID 1472769Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1472769
Br[C:2]1[CH:3]=[C:4]([C:8]#[N:9])[S:5][C:6]=1Br.[Cl:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[C:13]([CH3:20])[CH:12]=1.O1[CH2:26][CH2:25]OCC1.C(=O)([O-])[O-].[Na+].[Na+]>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.O>[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:3]=[C:4]([C:8]#[N:9])[S:5][C:6]=2[C:14]2[CH:13]=[CH:12][C:11]([Cl:10])=[CH:16][C:25]=2[CH3:26])=[C:13]([CH3:20])[CH:12]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 312751,4-DioxaneHCID 5017600(4-Chloro-2-methylphenyl)boronic acidHCID 232622764,5-Dibromothiophene-2-carbonitrile

Produkt 1

HCID 682936344,5-Bis(4-chloro-2-methylphenyl)thiophene-2-carbonitrileAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A round-bottomed flask was charged with 4,5-dibromothiophene-2-carbonitrile (534 mg, 2.00 mmol), 4-chloro-2-methylphenylboronic acid (818 mg, 4.80 mmol) and Pd(PPh3)4 (136 mg, 0.10 mmol). After degassed, dioxane (10 mL) and aqueous sodium carbonate (5 mL, 2M, 10 mmol) was added. The reaction mixture was heated to 90° C. The progress of the reaction was monitored by TLC. After the reaction was complete, 50 mL of water was added, and the reaction mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous sodium sulphate and then concentrated. The residue was purified by flash chromatography (hexane:CH2Cl2=2:1). 0.60 g (84%) of product was obtained as clear oil.

Aufarbeitung

  1. customAfter degassed
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe organic phase was dried over anhydrous sodium sulphate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (hexane:CH2Cl2=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-8bdaa99b9d2843429bd42ddfd2ead309
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09012655B2

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