Dimethylformamide → 5-Chloro-4-hydroxymethylthiophene-2-carbonitrile
Reaktionsgleichung
Br[C:2]1[S:6][C:5]([Cl:7])=[C:4]([CH2:8][OH:9])[CH:3]=1.[CH3:10][N:11](C)C=O>C(OCC)(=O)C.[C-]#N.[Zn+2].[C-]#N.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>[Cl:7][C:5]1[S:6][C:2]([C:10]#[N:11])=[CH:3][C:4]=1[CH2:8][OH:9]Komponenten
6
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 100 °C
Versuchsvorschrift
To a solution of 25.0 g (5-bromo-2-chlorothiophen-3-yl)methanol in 330 mL of dimethylformamide, 25.8 g of zinc cyanide (I) and 12.7 g tetrakis(triphenylphosphine)palladium(0) were added at room temperature, and stirred at 100° C. for 4 hours. Diluting with ethyl acetate, the organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:5), to afford 16.0 g of the title compound as colorless crystals.
Aufarbeitung
- washthe organic layer was washed successively with saturated aqueous ammonium chloride and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was evaporated
- customThe crude product was purified
- customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:5)
Quellen und Nachweise
- ORD-Eintrag
- ord-fe53eddbf6e24573b0d61b6749f23191
- Quelldatensatz
- uspto-grants-2008_09
- Patentnummer
- US07429609B2
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