Hydrochloric Acid → 4-Acetyl-2-fluorobenzonitrile

Temperatur

90 °C

A mixture of 5.0 g (0.02 mol) 4-bromo-2-fluorobenzonitrile, 6 ml TEA, 906 mg (0.0022 mol) dppp, 5.8 g (0.04 mol) TIOAc, and 448 mg (0.002 mol) Pd(OAc)2 in 50 ml DMF was deaired under a stream of N2 The mixture was heated to 90° C. for 7 hours. The reaction was cooled to room temperature and 25 mL 2N HCl was added and stirred to 30 minutes. The mixture was poured into 300 ml water and extracted with Et2O (2×300 mL). The combined organics were washed with water (2×80 mL), brine (1×80 mL), dried over MgSO4 and concentrated to give an oil, which was then chromatographed on silica gel eluted with 30% ethyl acetate/70% hexanes to give 2.5 g of a yellow/orange oil.

1. temperatureThe reaction was cooled to room temperature
2. extractionextracted with Et2O (2×300 mL)
3. washThe combined organics were washed with water (2×80 mL), brine (1×80 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. customto give an oil, which
7. customwas then chromatographed on silica gel
8. washeluted with 30% ethyl acetate/70% hexanes

ORD-Eintrag

ord-b274483724dd4b3e94d791cd1b8a9e69

Quelldatensatz

uspto-grants-2003_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06559168B2