Dimethylformamide → HCID 22996227, Verbindung

Temperatur

95 °C

To a solution of 1-bromo-4-methoxy-2-propoxy-benzene (500 mg, 2.04 mmol) in dimethylformamide (10 mL) at room temperature was added zinc cyanide (240 mg, 2.04 mmol). The reaction mixture was degassed by passing argon through for 2 h before tetrakis(triphenylphosphine)palladium (236 mg, 0.204 mmol) was added. The reaction mixture was heated at 90-100° C. under argon for 12 h. The reaction mixture was taken up in diethyl ether (10 mL) and sodium bicarbonate solution (2 mL). The product was extracted with diethyl ether (2×20 mL). The organic layers were washed with water (1×5 mL), brine (1×5 mL), and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 15-20% ethyl acetate in hexanes yielded 4-methoxy-2-propoxy-benzonitrile (290 mg, 74%) as white solids.

1. customThe reaction mixture was degassed
2. customthrough for 2 h
3. additionwas added
4. extractionThe product was extracted with diethyl ether (2×20 mL)
5. washThe organic layers were washed with water (1×5 mL), brine (1×5 mL)
6. dry with materialdried over anhydrous sodium sulfate
7. filtrationThe solid was then filtered off
8. concentrationthe filtrate was concentrated in vacuo
9. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
10. washeluting with 15-20% ethyl acetate in hexanes

ORD-Eintrag

ord-edad628ce2f84917a9920d775e20f723

Quelldatensatz

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06617346B1