Hydrochloric Acid → 2-Fluoro-5-[2-(trimethylsilyl)ethynyl]benzenebutanenitrile

Temperatur

85 °C

To a stirred solution of 4-(5-Bromo-2-fluoro-phenyl)-butyronitrile (0.37 g, 1.52 mmol) in diethyl amine (6 mL) and DMF (2 mL) was added triphenylphosine (0.08 g, 0.31 mmol), trimethylsilylacetylene (0.23 ml, 1.7 mmol), CuI (0.015 g, 0.076 mmol), and dichlorbis(triphenylphospine)palladium (0.054 g, 0.076 mmol). The reaction was heated at 85° C. for 12 h and then cooled to room temperature. The reaction was diluted with ethyl acetate (20 mL) and then poured into 0.1 N HCl (20 mL) and extracted with ethyl acetate (3×50 ml). The extracts were washed with water (10 mL) and brine (10 mL), dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography (5% to 10% ethyl acetate/petroleum ether) gave the title compound as a clear oil (0.28 g, 70%), identified by NMR and mass spectral analyses; MS (ES+): 260 (M+H).

1. temperaturecooled to room temperature
2. extractionextracted with ethyl acetate (3×50 ml)
3. washThe extracts were washed with water (10 mL) and brine (10 mL)
4. dry with materialdried (MgSO4)
5. concentrationconcentrated in vacuo
6. customPurification by flash chromatography (5% to 10% ethyl acetate/petroleum ether)

ORD-Eintrag

ord-18229ee87e7841919d5bf83793a2463e

Quelldatensatz

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07723368B2