Toluene → 4-(4-(4-Methoxyphenyl)thiophen-3-yl)-3-methylbenzonitrile

HRID 536604

Reaktionsgleichung

Reaktionsgleichung von HRID 536604
Br[C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[CH:5][S:4][CH:3]=1.[C:15]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[C:19]([CH3:26])[CH:18]=1)#[N:16].C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C(O)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>[CH3:14][O:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]2[C:2]([C:20]3[CH:21]=[CH:22][C:17]([C:15]#[N:16])=[CH:18][C:19]=3[CH3:26])=[CH:3][S:4][CH:5]=2)=[CH:8][CH:9]=1

Komponenten

8

Edukt 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 106595733-Bromo-4-(4-methoxyphenyl)thiopheneHCID 16218401(4-Cyano-2-methyl-phenyl)boronic acid

Produkt 1

HCID 672536684-(4-(4-Methoxyphenyl)thiophen-3-yl)-3-methylbenzonitrileAusbeute 69,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a mixture of 3-bromo-4-(4-methoxyphenyl)thiophene (Scheme I, 2, X1=4-methoxyphenyl) (1.7 g, 6.316 mmol), 4-cyano-2-methylphenylboronic acid (Scheme I, 2A, X2=4-cyano-2-methylphenyl) (1.535 g, 6.316 mmol), sodium carbonate (1.34 g, 12.63 mmol), toluene (60 mL) in a mixture of ethanol (36 mL) and water (24 mL) under nitrogen was added Pd(PPh3)4 (0.7 g, 0.606 mmol). The mixture was stirred at 80° C. for 5 h, poured into water (50 mL), and extracted with ethyl acetate (50 mL×3). The organic extracts were dried over anhydrous magnesium sulfate (6 g), evaporated, and purified by column chromatography on silica gel (petroleum ether/ethyl acetate=50:1) to give 4-(4-(4-methoxyphenyl)thiophen-3-yl)-3-methylbenzonitrile (Scheme I, 3, X1=4-methoxyphenyl, X2=4-cyano-2-methylphenyl) (1.34 g, yield 69.4%). 1H NMR (DMSO-d6 400 MHz): δ 7.68-7.65 (m, 3H), 7.58 (d, J=3.2 Hz, 1H), 7.33 (d, J=8.0 Hz, 1H), 6.98 (d, J=8.8 Hz, 2H), 6.80 (d, J=8.8 Hz, 2H), 3.70 (s, 3H), 1.79 (s, 3H).

Aufarbeitung

  1. extractionextracted with ethyl acetate (50 mL×3)
  2. dry with materialThe organic extracts were dried over anhydrous magnesium sulfate (6 g)
  3. customevaporated
  4. custompurified by column chromatography on silica gel (petroleum ether/ethyl acetate=50:1)

Quellen und Nachweise

ORD-Eintrag
ord-1e65a6e1630543a5ad32e46ad63a5698
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08859611B2

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